Abstract
This review, including 245 references, describes the application of Lawesson’s reagent
[2,4-bis(p -methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulfide] LR in organic and organometallic syntheses. Thionations of carbonyl-containing compounds
as well as unexpected reactions are shown for different applications (e.g. cyclizations,
rerrangements, syntheses of heterocyclic compounds etc.). Syntheses of novel organometallic
compounds by LR are also discussed.
1 Introduction
2 Mechanism of the Thionation Reaction Using Lawesson’s Reagent
3 Reactions with Carbonyl-Containing Compounds
3.1 Ketones
3.2 Esters and Lactones
3.3 Amides and Lactams
3.4 Amino Acids, Peptides, Nucleosides, and Nucleotides
3.5 Macrocycles and Polymers
4 Cyclization Reactions to Thiophenes, Thiazoles and Other Compounds
5 Synthesis of Heteroatom-Containing Compounds
5.1 Sulfur-Containing Heterocyclic Compounds
5.2 Phosphorus- and Sulfur-Containing Heterocycles
5.3 Other Phosphorus- and Sulfur-Containing Compounds
6 Synthesis of Organometallic Compounds
6.1 Transition Metals
6.2 Main Group Metals
7 Usage of Lawesson’s Reagent for Special Syntheses
7.1 Glycosidations
7.2 Transformation of Alcohols to Thiols
7.3 Reduction of Sulfoxides
7.4 Catalyst for Aldol Reactions
7.5 Preparation of Other Compounds
8 Unexpected Reactions Following the Usage of Lawesson’s Reagent
9 References
Key words
Lawesson’s reagent - thionation - organothiophosphorus reagent - heterocycles - sulfur-compounds
- organometallic compounds
References
<A NAME="RE09203SS-1">1 </A>
Campaigne E.
Chem. Rev.
1946,
1:
39
<A NAME="RE09203SS-2">2 </A>
Schobel A.
Wagner A. In
Methoden der organischen Chemie (Houben-Weyl)
Müller M.
Thieme;
Stuttgart:
1955.
Vol. IX E..
p.699
<A NAME="RE09203SS-3">3 </A>
Reid EE. In Organic Chemistry of Bivalent Sulfur
Vol. 3, Chap. 2:
Chem. Pub.;
New York:
1960.
<A NAME="RE09203SS-4">4 </A>
Campaigne E. In The Chemistry of the Carbonyl Group
Chap. 17:
Patai S.
Interscience;
New York:
1966.
<A NAME="RE09203SS-5">5 </A>
Oae S.
Nakanishi A.
Tsujimoto N.
Chem. Ind. (London)
1972,
575
<A NAME="RE09203SS-6">6 </A>
Dean FM.
Goodchild J.
Hill AW.
J. Chem. Soc. (C)
1969,
2192
<A NAME="RE09203SS-7">7 </A>
Dean FM.
Goodchild J.
Hill AW.
J. Chem. Soc. (C)
1969,
12
<A NAME="RE09203SS-8">8 </A>
Perregaard J.
Scheibye S.
Meyer HJ.
Thomsen I.
Lawesson SO.
Bull. Soc. Chim. Belg.
1977,
86:
679
<A NAME="RE09203SS-9">9 </A>
Ten Hoeve W.
Wynberg H.
Havinga EE.
Meijer EW.
J. Am. Chem. Soc.
1991,
113:
5888
<A NAME="RE09203SS-10">10 </A>
Lecher HZ.
Greenwood RA.
Whitehouse KC.
Chao TH.
J. Am. Chem. Soc.
1956,
78:
5018
<A NAME="RE09203SS-11">11 </A>
Fay P.
Lankelma HP.
J. Am. Chem. Soc.
1952,
74:
4933
<A NAME="RE09203SS-12">12 </A>
Hoffman H.
Schumacher G.
Tetrahedron Lett.
1967,
8:
2963
<A NAME="RE09203SS-13">13 </A>
Pedersen BS.
Scheibye S.
Nilsson NH.
Lawesson
S.-O.
Bull. Soc. Chim. Belg.
1978,
87:
223
<A NAME="RE09203SS-14">14 </A>
Mazitova FN.
Khairullin VK.
Zh. Org. Khim.
1981,
51:
958
<A NAME="RE09203SS-15">15 </A>
Hitotsuyanagi Y.
Suzuki J.
Matsumoto Y.
Takeya K.
Itokawa H.
J. Chem. Soc., Perkin Trans. 1
1994,
1887
<A NAME="RE09203SS-16">16 </A>
Grisenti P.
Magni A.
Manzocchi A.
Ferraboschi P.
Steroids
1997,
62:
504
<A NAME="RE09203SS-17">17 </A>
Fossey C.
Landelle H.
Laduree D.
Robba M.
Nucleosides Nucleotides
1993,
12:
973
<A NAME="RE09203SS-18">18 </A>
Levinson MI.
Cava MP.
Tetrahedron
1985,
41:
5061
<A NAME="RE09203SS-19">19 </A>
Cherkasov RA.
Kutyrev GA.
Pudovik AN.
Tetrahedron
1985,
41:
2567
<A NAME="RE09203SS-20">20 </A>
Milewska MJ.
Chemia
2000,
46:
3
<A NAME="RE09203SS-21">21 </A>
Liangnian H.
Cai F.
Li K.
Huaxue Shiji
1999,
21:
22 ; Chem. Abstr. 1999 , 130 , 325163
<A NAME="RE09203SS-22">22 </A>
Aimakov OA.
Mastryukova TA.
Erzhanov KV.
Seriya Khimicheskaya
1998,
53 ; Chem. Abstr. 1998 , 133 , 281654
<A NAME="RE09203SS-23">23 </A>
Li Y.-G.
Zhu X.-F.
Zhou H.-J.
Youji Huaxue
1995,
15:
461 ; Chem. Abstr. 1995 , 123 , 338589
<A NAME="RE09203SS-24">24 </A>
Chen J.
Huaxue Shiji
1988,
10:
156 ; Chem. Abstr. 1988 , 110 , 38281
<A NAME="RE09203SS-25">25 </A>
Tang C.
Youji Huaxue
1988,
8:
80 ; Chem. Abstr. 1988 , 109 , 6555
<A NAME="RE09203SS-26">26 </A>
El-Barbary AA.
Monatsh. Chem.
1984,
115:
769
<A NAME="RE09203SS-27">27 </A>
Foreman M St. J.
Slawin AMZ.
Woolins JD.
Heteroatom Chem.
1999,
10:
651
<A NAME="RE09203SS-28">28 </A>
Barner-Kowollik C.
Davis TP.
Heuts JPA.
Stenzel MH.
Vana P.
Whittaker M.
J. Pol. Sci., Part A: Pol. Chem.
2003,
41:
365
<A NAME="RE09203SS-29">29 </A>
Chiefari J.
Chong YK.
Ercole F.
Krstina J.
Jeffery J.
Le TPT.
Mayadunne RTA.
Meijs GF.
Moad CL.
Moad G.
Rizzardo E.
Thang SH.
Macromolecules
1998,
31:
5559
<A NAME="RE09203SS-30">30 </A>
Scheibye S.
Pedersen BS.
Lawesson S.-O.
Bull. Soc. Chim. Belg.
1978,
87:
229
<A NAME="RE09203SS-31">31 </A>
Fluck E.
Binder H.
Z. Anorg. Allg. Chem.
1967,
354:
113
<A NAME="RE09203SS-32">32 </A>
Scheibye S.
Shabana R.
Lawesson S.-O.
Romming C.
Tetrahedron
1982,
38:
993
<A NAME="RE09203SS-33">33 </A>
Kametani S.
Ohmura O.
Tanaka H.
Motoki S.
Chem. Lett.
1982,
793
<A NAME="RE09203SS-34">34 </A>
Bertrand G.
Majoral JP.
Baceiredo A.
Tetrahedron Lett.
1980,
21:
5015
<A NAME="RE09203SS-35">35 </A>
Westheimer FH.
Chem. Rev.
1981,
81:
313
<A NAME="RE09203SS-36">36 </A>
Regitz M.
Maas G.
Org. Chem. Berlin
1981,
71
<A NAME="RE09203SS-37">37 </A>
Pedersen BS.
Lawesson S.-O.
Tetrahedron
1979,
35:
2433
<A NAME="RE09203SS-38">38 </A>
Shabana R.
Scheibye S.
Clausen K.
Olesen SO.
Lawesson S.-O.
New J. Chem.
1980,
4:
47
<A NAME="RE09203SS-39">39 </A>
Corbridge DEC.
Phosphorus An Outline of its Chemistry Biochemistry and Technology
Elsevier;
Amsterdam:
1980.
<A NAME="RE09203SS-40">40 </A>
Navech J.
Majoral JP.
Kraemer R.
Tetrahedron Lett.
1983,
24:
5885
<A NAME="RE09203SS-41">41 </A>
Rauchfuss TB.
Zank GA.
Tetrahedron Lett.
1986,
27:
3445
<A NAME="RE09203SS-42">42 </A>
Yoshifuji M.
An D.-L.
Toyota K.
Yasunami M.
Tetrahedron Lett.
1994,
35:
4379
<A NAME="RE09203SS-43">43 </A>
Nakai T.
McDowell CA.
Solid State Nucl. Magn. Reson.
1995,
4:
163
<A NAME="RE09203SS-44">44 </A>
Baxter L.
Bradshaw JS.
J. Org. Chem.
1981,
46:
831
<A NAME="RE09203SS-45">45 </A>
Varma RS.
Kumar D.
Org. Lett.
1999,
1:
697
<A NAME="RE09203SS-46">46 </A>
Baruah AK.
Prajapati D.
Sandhu JS.
Tetrahedron
1988,
44:
6137
<A NAME="RE09203SS-47">47 </A>
Baker W.
Harborne JB.
Ollis WD.
J. Chem. Soc.
1952,
1303
<A NAME="RE09203SS-48">48 </A>
Baker W.
Clarke GG.
Harbone JB.
J. Chem. Soc.
1954,
998
<A NAME="RE09203SS-49">49 </A>
Weiß D.
Gaudig U.
Beckert R.
Synthesis
1992,
751
<A NAME="RE09203SS-50">50 </A>
Kim SH.
Han SK.
Kim JJ.
Hwang SH.
Yoon CM.
Keum SR.
Dyes Pigments
1998,
39:
77
<A NAME="RE09203SS-51">51 </A>
Strehlow T.
Voß J.
Spohnholz R.
Adieidjaja G.
Chem. Ber.
1991,
1397
<A NAME="RE09203SS-52">52 </A>
Horner L.
Lindel H.
Phosphorus Sulfur
1982,
12:
259
<A NAME="RE09203SS-53">53 </A>
Quin LD.
Osman FH.
Day RO.
Hughes AN.
Wu X.-P.
Wang L.-Q.
New J. Chem.
1989,
13:
375
<A NAME="RE09203SS-54">54 </A>
Kawashima T.
Kojima S.
Inamoto N.
Chem. Lett.
1989,
849
<A NAME="RE09203SS-55">55 </A>
Piettre SR.
Tetrahedron Lett.
1996,
37:
4707
<A NAME="RE09203SS-56">56 </A>
Piettre SR.
Raboisson P.
Tetrahedron Lett.
1996,
37:
2229
<A NAME="RE09203SS-57">57 </A>
Polozov AM.
Cremer SE.
Fanwick PE.
Can. J. Chem.
1999,
77:
1274
<A NAME="RE09203SS-58">58 </A>
Iwanaga H.
Naito K.
Sunohara K.
Okajima M.
Bull. Chem. Soc. Jpn.
1998,
71:
1719
<A NAME="RE09203SS-59">59 </A>
Nawwar GAM.
Haggag BM.
Yakout El-SMA.
Z. Naturforsch., B: Chem. Sci.
1992,
47:
1639
<A NAME="RE09203SS-60">60 </A>
Lee HK.
Kim J.
Pak CS.
Tetrahedron Lett
1999,
40:
6267
<A NAME="RE09203SS-61">61 </A>
Nicolaou KC.
Hwang C.-K.
Marron BE.
DeFrees SA.
Couladouros EA.
Abe Y.
Carroll PJ.
Snyder JP.
J. Am. Chem. Soc.
1990,
112:
3040
<A NAME="RE09203SS-62">62 </A>
Peters K.
Peters E.-M.
Bringmann G.
Schupp O.
Z. Naturforsch, B: Chem. Sci.
1996,
51:
431
<A NAME="RE09203SS-63">63 </A>
Bringmann G.
Wuzik A.
Schupp O.
Peters K.
Peters E.-M.
Z. Naturforsch., B: Chem. Sci.
1997,
52:
355
<A NAME="RE09203SS-64">64 </A>
Kahne D.
Yang D.
Lim JJ.
Miller R.
Paguaga E.
J. Am. Chem. Soc.
1988,
110:
8716
<A NAME="RE09203SS-65">65 </A>
Olsson R.
Hansen HC.
Andersson C.-M.
Tetrahedron Lett.
2000,
41:
7947
<A NAME="RE09203SS-66">66 </A>
Pons J.-F.
Mishir Q.
Nouvet A.
Brookfield F.
Tetrahedron Lett.
2000,
41:
4965
<A NAME="RE09203SS-67">67 </A>
Blass BE.
Coburn KR.
Faulkner AL.
Liu S.
Ogden A.
Portlock DE.
Srivastava A.
Tetrahedron Lett.
2002,
43:
8165
<A NAME="RE09203SS-68">68 </A>
Pedersen BS.
Scheibye S.
Clausen K.
Lawesson S.-O.
Bull. Soc. Chim. Belg.
1978,
87:
293
<A NAME="RE09203SS-69">69 </A>
Seebach D.
Ko SY.
Kessler H.
Köck M.
Reggelin M.
Schmieder P.
Walkinshaw MD.
Bölsterli JJ.
Bevec D.
Helv. Chim. Acta
1991,
74:
1953
<A NAME="RE09203SS-70">70 </A>
Wang L.
Phanstiel O.
J. Org. Chem.
2000,
65:
1442
<A NAME="RE09203SS-71">71 </A>
Jensen OE.
Lawesson S.-O.
Bardi R.
Piazzesi AM.
Toniolo C.
Tetrahedron
1985,
41:
5595
<A NAME="RE09203SS-72">72 </A>
Morita H.
Nagashima S.
Takeya K.
Itokawa H.
J. Chem. Soc., Perkin Trans. 1
1995,
2327
<A NAME="RE09203SS-73">73 </A>
Morita H.
Nagashima S.
Takeya K.
Itokawa H.
Bioorg. Med. Chem. Lett.
1995,
5:
677
<A NAME="RE09203SS-74">74 </A>
Morita H.
Yun YS.
Takeya K.
Itokawa H.
Shirota O.
Bioorg. Med. Chem.
1997,
5:
631
<A NAME="RE09203SS-75">75 </A>
Guziec FS.
Mayer Wasmund L.
J. Chem. Res., Synop.
1989,
155
<A NAME="RE09203SS-76">76 </A>
G uziec FS.
Mayer Wasmund L.
J. Chem. Res., Miniprint
1989,
1301
<A NAME="RE09203SS-77">77 </A>
Yokoyama M.
Hasegawa Y.
Hatanaka H.
Kawazoe Y.
Imamoto T.
Synthesis
1984,
827
<A NAME="RE09203SS-78">78 </A>
Larsen C.
Kragh H.
Rasmussen PB.
Andersen TP.
Senning A.
Liebigs Ann. Chem.
1989,
819
<A NAME="RE09203SS-79">79 </A>
Pedersen U.
Thorsen M.
El-Khrisy E.-EAM.
Clausen K.
Lawesson S.-O.
Tetrahedron
1982,
38:
3267
<A NAME="RE09203SS-80">80 </A>
Thorsen M.
Andersen TP.
Pedersen U.
Yde B.
Lawesson S.-O.
Tetrahedron
1985,
41:
5633
<A NAME="RE09203SS-81">81 </A>
Jensen OE.
Lawesson S.-O.
Tetrahedron
1985,
41:
5595
<A NAME="RE09203SS-82">82 </A>
Petrie CR.
Revankar GR.
Dalley NK.
George RD.
McKernan PA.
Hamill RL.
Robins RK.
J. Med. Chem.
1986,
29:
268
<A NAME="RE09203SS-83">83 </A>
Rico-Gómez R.
Ruiz-Mora ML.
de Inestrosa Villatoro EP.
Rios-Ruiz J.
Heterocycles
1988,
27:
13
<A NAME="RE09203SS-84">84 </A>
Jørgensen PT.
Pedersen EB.
Nielsen C.
Synthesis
1992,
1299
<A NAME="RE09203SS-85">85 </A>
Felczak K.
Bretner M.
Kulikowski T.
Shugar D.
Nucleosides Nucleotides
1993,
12:
245
<A NAME="RE09203SS-86">86 </A>
Brunner A.
Kühnle FNM.
Seebach D.
Helv. Chim. Acta
1996,
79:
319
<A NAME="RE09203SS-87">87 </A>
Clyne DS.
Weiler L.
Tetrahedron
1999,
55:
13659
<A NAME="RE09203SS-88">88 </A>
Delêtre M.
Levesque G.
Macromolecules
1990,
23:
4876
<A NAME="RE09203SS-89">89 </A>
Wang ZY.
Zhang C.
Macromolecules
1992,
25:
5851
<A NAME="RE09203SS-90">90 </A>
Zhang C.
Wang ZY.
Macromolecules
1993,
26:
3330
<A NAME="RE09203SS-91">91 </A>
Wang ZY.
Zhang C.
Arnoux F.
Macromolecules
1994,
27:
4415
<A NAME="RE09203SS-92">92 </A>
Wang ZY.
Franklin J.
Venkatesan D.
Wang Y.
Macromolecules
1999,
32:
1691
<A NAME="RE09203SS-93">93 </A>
Steliou K.
Salama P.
Yu X.
J. Am. Chem. Soc.
1992,
114:
1456
<A NAME="RE09203SS-94">94 </A>
Sato M.
Yamauchi K.
Handa M.
Kasuga KI.
Macromol. Rapid Commun.
2000,
21:
1234
<A NAME="RE09203SS-95">95 </A>
Pouwer KL.
Vries TR.
Havinga EE.
Meijer EW.
Wynberg H.
J. Chem. Soc., Chem. Commun.
1988,
1432
<A NAME="RE09203SS-96">96 </A>
Hempenius MA.
Langeveld-Voss BMW.
van Haare JAEH.
Janssen RAJ.
Sheiko SS.
Spatz JP.
Möller M.
Meijer EW.
J. Am. Chem. Soc.
1998,
120:
2798
<A NAME="RE09203SS-97">97 </A>
Herbert MR.
Sonpatki VM.
Jakli A.
Seed AJ.
Mol. Cryst. Liq. Cryst.
2001,
365, 181
<A NAME="RE09203SS-98">98 </A>
Sonpatki VM.
Herbert MR.
Sandvoss LM.
Seed AJ.
J. Org. Chem.
2001,
66:
7283
<A NAME="RE09203SS-99">99 </A>
Kiryanov AA.
Sampson P.
Seed AJ.
J. Org. Chem.
2001,
66:
7925
<A NAME="RE09203SS-100">100 </A>
Lichtenthaler FW.
Brust A.
Cuny E.
Green Chem.
2001,
3:
201
<A NAME="RE09203SS-101">101 </A>
Joshi MVJ.
Hemler C.
Cava MP.
Cain JL.
Bakker MG.
McKinley AJ.
Metzger RM.
J. Chem. Soc., Perkin Trans. 2
1993,
1081
<A NAME="RE09203SS-102">102 </A>
Nishio T.
Helv. Chim. Acta
1998,
81:
1207
<A NAME="RE09203SS-103">103 </A>
Merz A.
Ellinger F.
Synthesis
1991,
462
<A NAME="RE09203SS-104">104 </A>
Johnson MR.
Miller DC.
Bush K.
Becker JJ.
Ibers JA.
J. Org. Chem.
1992,
57:
4414
<A NAME="RE09203SS-105">105 </A>
Ong CW.
Chen CM.
Wang LF.
Tetrahedron Lett.
1998,
39:
9191
<A NAME="RE09203SS-106">106 </A>
Ueda M.
Hayakawa T.
Haba O.
Macromolecules
1997,
30:
7069
<A NAME="RE09203SS-107">107 </A>
Schweiger LF.
Ryder KS.
Morris DG.
Glidle A.
Cooper JM.
J. Mater. Chem.
2000,
10:
107
<A NAME="RE09203SS-108">108 </A>
Jeong H.-J.
Kobayashi A.
Kakimoto A.
Imai Y.
Polym. J.
1994,
26:
99
<A NAME="RE09203SS-109">109 </A>
Nishio T.
Okuda N.
Kashima C.
J. Heterocycl. Chem.
1988,
25:
1437
<A NAME="RE09203SS-110">110 </A>
Bäuerle P.
Götz G.
Emerle P.
Port H.
Adv. Mater.
1992,
4:
564
<A NAME="RE09203SS-111">111 </A>
Noe CR.
Knollmüller M.
Wagner E.
Monatsh. Chem.
1986,
117:
621
<A NAME="RE09203SS-112">112 </A>
Ishii A.
Nakayama J.
Kazami J.
Ida Y.
Nakamura T.
Hoshino M.
J. Org. Chem.
1991,
56:
78
<A NAME="RE09203SS-113">113 </A>
Omar MT.
El-Khamry A.
Youssef AM.
Ramadan S.
Sulfur Lett.
2002,
25:
173
<A NAME="RE09203SS-114">114 </A>
Kang K.-T.
Sun UJ.
Synth. Commun.
1995,
25:
2647
<A NAME="RE09203SS-115">115 </A>
Kim EK.
Lee KU.
Cho BY.
Kim YB.
Kang K.-T.
Liquid Crystals
2001,
28:
339
<A NAME="RE09203SS-116">116 </A>
Hörndler C.
Hansen HJ.
Helv. Chim. Acta
1997,
80:
2520
<A NAME="RE09203SS-117">117 </A>
Lin S.-C.
Yang F.-D.
Shiue J.-S.
Yang S.-M.
Fang J.-M.
J. Org. Chem.
1998,
63:
2909
<A NAME="RE09203SS-118">118 </A>
Ozturk T.
Tetrahedron Lett.
1996,
37:
2821
<A NAME="RE09203SS-119">119 </A>
Ozturk T.
Wallis JD.
Acta Crystallogr., Sect. C
1996,
52:
2552
<A NAME="RE09203SS-120">120 </A>
Kaynak FB.
Özbey S.
Ötztürk T.
Ertas E.
Acta Crystallogr., Sect. C
2001,
57:
1125
<A NAME="RE09203SS-121">121 </A>
Zhang W.
Henry Y.
Synlett
2001,
1129
<A NAME="RE09203SS-122">122 </A>
Closs F.
Srdanov G.
Wudl F.
J. Chem. Soc., Chem Commun.
1989,
1716
<A NAME="RE09203SS-123">123 </A>
Karakasa T.
Satsumabayashi S.
Motoki S.
Bull. Chem. Soc. Jpn.
1986,
59:
335
<A NAME="RE09203SS-124">124 </A>
Karakasa T.
Moriyama S.
Motoki S.
Chem. Lett.
1988,
1029
<A NAME="RE09203SS-125">125 </A>
Moriyama S.
Motoki S.
Bull. Chem. Soc. Jpn.
1992,
65:
2056
<A NAME="RE09203SS-126">126 </A>
Hegab MIM.
Phosphorus, Sulfur Silicon Relat. Elem.
2000,
166:
137
<A NAME="RE09203SS-127">127 </A>
Rufanov KA.
Stepanov AS.
Lemenovski DA.
Churakov AV.
Heteroatom Chem.
1999,
10:
369
<A NAME="RE09203SS-128">128 </A>
Nakayama J.
Nakamura Y.
Murabayashi S.
Hoshino M.
Heterocycles
1987,
26:
939
<A NAME="RE09203SS-129">129 </A>
Ishii A.
Omata T.
Umezawa K.
Nakayama J.
Bull. Chem. Soc. Jpn
2000,
73:
729
<A NAME="RE09203SS-130">130 </A>
Nishio T.
Sekiguchi H.
Tetrahedron
1999,
55:
5017
<A NAME="RE09203SS-131">131 </A>
Nishio T.
Tetrahedron Lett.
1995,
36:
6113
<A NAME="RE09203SS-132">132 </A>
Nishio T.
Ori M.
Helv. Chim. Acta
2001,
84:
2347
<A NAME="RE09203SS-133">133 </A>
Uchikawa O.
Fukatsu K.
Aono TJ.
Heterocycl. Chem.
1994,
31:
877
<A NAME="RE09203SS-134">134 </A>
Jenny C.
Heimgartner H.
Helv. Chim. Acta
1986,
69:
374
<A NAME="RE09203SS-135">135 </A>
Thompson DK.
Suzuki N.
Hegedus LS.
Satoh Y.
J. Org. Chem.
1992,
57:
1461
<A NAME="RE09203SS-136">136 </A>
Fruit C.
Turck A.
Ple N.
Queguiner G.
J. Heterocycl. Chem.
2002,
39:
1077
<A NAME="RE09203SS-137">137 </A>
Nishio T.
J. Org. Chem.
1997,
62:
1106
<A NAME="RE09203SS-138">138 </A>
Savarino P.
Viscardi G.
Carpignano R.
Borda A.
Barni E.
J. Heterocycl. Chem.
1989,
26:
289
<A NAME="RE09203SS-139">139 </A>
Gordon TD.
Singh J.
Hansen PE.
Morgan BA.
Tetrahedron Lett.
1993,
34:
1901
<A NAME="RE09203SS-140">140 </A>
Jenny C.
Heimgartner H.
Helv. Chim. Acta
1989,
72:
1639
<A NAME="RE09203SS-141">141 </A>
Soto JL.
Seoane C.
Rubio MJ.
Botija JM.
Org. Prep. Proced. Int.
1984,
16:
11
<A NAME="RE09203SS-142">142 </A>
Milewska MJ.
Bytner T.
Polonski T.
Synthesis
1996,
1485
<A NAME="RE09203SS-143">143 </A>
Tschierske C.
Girdziunaite D.
J. Prakt. Chem.
1991,
333:
135
<A NAME="RE09203SS-144">144 </A>
Nishio T.
Konno Y.
Ori M.
Sakamoto M.
Eur. J. Org. Chem.
2001,
3553
<A NAME="RE09203SS-145">145 </A>
Lee J.
Hong SI.
Macromol. Chem. Phys.
1997,
198:
391
<A NAME="RE09203SS-146">146 </A>
Kotian P.
Mascarella W.
Abraham P.
Lewin AH.
Boja JW.
Kuhar MJ.
Carroll FI.
J. Med. Chem.
1996,
39:
2753
<A NAME="RE09203SS-147">147 </A>
Tully WR.
Gardner CR.
Gillespie RJ.
Westwood R.
J. Med. Chem.
1993,
34:
2060
<A NAME="RE09203SS-148">148 </A>
Bochu C.
Couture A.
Grandclaudon P.
J. Org. Chem.
1988,
53:
4852
<A NAME="RE09203SS-149">149 </A>
Kamitori Y.
Hojo M.
Masuda R.
Kawamura Y.
Numai T.
Synthesis
1990,
491
<A NAME="RE09203SS-150">150 </A>
Mitra RB.
Muljiani Z.
Deshpande SR.
Heterocycles
1988,
27:
2297
<A NAME="RE09203SS-151">151 </A>
Charrier J.-D.
Reliquet A.
Meslin JC.
Tetrahedron: Asymmetry
1998,
9:
1531
<A NAME="RE09203SS-152">152 </A>
El-Barbary AA.
Hammouda HA.
El-Borai M.
Indian J. Chem., Sect. B
1984,
23:
770
<A NAME="RE09203SS-153">153 </A>
Adam W.
Hasemann L.
Chem. Ber.
1990,
123:
1449
<A NAME="RE09203SS-154">154 </A>
Khidre MD.
Yakout EMA.
Refat M.
Mahran H.
Phosphorus, Sulfur Silicon Relat. Elem.
1998,
133:
119
<A NAME="RE09203SS-155">155 </A>
Ibrahim YA.
Kadry AM.
Ibrahim MR.
Lisgarten JN.
Potter BS.
Palmer RA.
Tetrahedron
1999,
55:
13457
<A NAME="RE09203SS-156">156 </A>
He L.-N.
Zhuo R.-X.
Synth. Commun.
1997,
27:
2853
<A NAME="RE09203SS-157">157 </A>
Shabana R.
Osman FH.
Atrees SS.
Tetrahedron Lett.
1994,
50:
6975
<A NAME="RE09203SS-158">158 </A>
Quast H.
Aldenkortt S.
Heller E.
Schäfer P.
Schmitt E.
Chem. Ber.
1994,
127:
1699
<A NAME="RE09203SS-159">159 </A>
Boulos LS.
Abd-El-Malek HA.
Heteroatom Chem.
1999,
10:
488
<A NAME="RE09203SS-160">160 </A>
Deng SL.
Liu DZ.
Chen RY.
Chin. Chem. Lett.
2001,
12:
1065
<A NAME="RE09203SS-161">161 </A>
Deng S.-L.
Liu D.-Z.
Huang J.-M.
Chen R.-Y.
Weng L.-H.
Leng X.-B.
Jiegou Huaxue (Chin. J. Struct. Chem.)
2002,
21:
46 ; Chem. Abstr. 2002 , 136 , 340748
<A NAME="RE09203SS-162">162 </A>
Deng SL.
Chen RY.
Synthesis
2002,
2527
<A NAME="RE09203SS-163">163 </A>
Sarma CS.
Kataky JCS.
Indian J. Chem., Sect B
1999,
38:
364
<A NAME="RE09203SS-164">164 </A>
Ghattas A.-BAG.
Abd-Allah OA.
Moustafa HM.
Phosphorus, Sulfur Siliconn Relat. Elem.
2000,
157:
1
<A NAME="RE09203SS-165">165 </A>
Deng S.-L.
Liu D.-Z.
Li W.
Jiegou Huaxue (Chin. J. Struct. Chem.)
2002,
21:
359 ; Chem. Abstr. 2002 , 565340
<A NAME="RE09203SS-166">166 </A>
Deng SL.
Liu DZ.
Synthesis
2001,
2445
<A NAME="RE09203SS-167">167 </A>
He L.-N.
Liu X.-P.
Luo Y.-P.
Lu A.-H.
Ding M.-W.
Phosphorus, Sulfur Silicon Relat. Elem.
2000,
158:
117
<A NAME="RE09203SS-168">168 </A>
He L.-N.
Zhuo R.-X.
Chen R.-Y.
Li K.
Zhang Y.-J.
Heteroatom Chem.
1999,
10:
105
<A NAME="RE09203SS-169">169 </A>
He L.-N.
Zhuo R.-X.
Liu X.-P.
Cai F.
Phosphorus, Sulfur Silicon Relat. Elem.
1999,
144-146:
453
<A NAME="RE09203SS-170">170 </A> See ref. 168
<A NAME="RE09203SS-171">171 </A>
He LN.
Chen R.-Y.
Phosphorus, Sulfur Silicon Relat. Elem.
1997,
129:
111
<A NAME="RE09203SS-172">172 </A>
He L.-N.
Li K.
Luo Y.-P.
Liu X.-P.
Ding M.-W.
Zhou Q.-C.
Wu T.-J.
Cai F.
Phosphorus, Sulfur Silicon Relat. Elem.
2000,
156:
173
<A NAME="RE09203SS-173">173 </A>
He LN.
Luo Y.
Ding M.
Lu A.
Liu X.
Wu T.
Cai F.
Heteroatom Chem.
2001,
12:
497
<A NAME="RE09203SS-174">174 </A>
Baruah P.
Kataky JCS.
Indian J. Heterocycl. Chem.
1998,
8:
43
<A NAME="RE09203SS-175">175 </A>
Deng S.-L.
Liu D.-Z.
Li W.
Acta Crystallogr., Sect.E
2002,
58:
1430
<A NAME="RE09203SS-176">176 </A>
Boulos LS.
Hennawy IT.
Arsanious HN.
Heteratom Chem.
1994,
5:
27
<A NAME="RE09203SS-177">177 </A>
Hegab MI.
El-Essawy FAG.
Madsen JO.
Sotofte I.
Senning A.
Sulfur Letters
2001,
24:
191
<A NAME="RE09203SS-178">178 </A>
Dubau-Assibat N.
Baceiredo A.
Bertrand G.
J. Org. Chem.
1995,
60:
3904
<A NAME="RE09203SS-179">179 </A>
He L.-N.
Chen R.-Y.
Heterocyl. Commun.
1997,
3:
461
<A NAME="RE09203SS-180">180 </A>
Testa MG.
Perrini G.
Chiacchio U.
Corsaro A.
Phosphorus, Sulfur Silicon Relat. Elem.
1994,
86:
75
<A NAME="RE09203SS-181">181 </A>
Hafez TS.
Atta SMS.
Fahmy AA.
Mahran MRH.
Sulfur Lett.
1993,
16:
257
<A NAME="RE09203SS-182">182 </A>
He LN.
Zhuo RX.
Chin. Chem. Lett.
1997,
8:
655
<A NAME="RE09203SS-183">183 </A>
Shabana R.
Yakout EM.
Atrees SS.
Heteroatom Chem.
1993,
4:
491
<A NAME="RE09203SS-184">184 </A>
He L.
Luo Y.
Li K.
Ding M.
Lu A.
Liu X.
Wu T.
Cai F.
Synth. Commun.
2002,
32:
1415
<A NAME="RE09203SS-185">185 </A>
Bryce MR.
Matthews RS.
J. Organomet. Chem.
1987,
325:
153
<A NAME="RE09203SS-186">186 </A>
Piquet V.
Baceiredo A.
Gornitzka H.
Dahan F.
Bertrand G.
Chem.-Eur. J.
1997,
3:
1757
<A NAME="RE09203SS-187">187 </A>
He L.-N.
Li K.
Liu X.-P.
Wu T.-J.
Luo Y.-P.
Hetercycl. Commun.
1998,
4:
451
<A NAME="RE09203SS-188">188 </A>
Moustafa HM.
Phosphorus, Sulfur Silicon Relat. Elem.
1999,
148:
131
<A NAME="RE09203SS-189">189 </A>
Moustafa HM.
Phosphorus, Sulfur Silicon Relat. Elem.
2000,
164:
11
<A NAME="RE09203SS-190">190 </A>
Shabana R.
Yousif NM.
Lawesson S.-O.
Phosphorus Sulfur Relat. Elem.
1985,
24:
327
<A NAME="RE09203SS-191">191 </A>
Shabana R.
Phosphorus Sulfur Relat. Elem.
1987,
29:
293
<A NAME="RE09203SS-192">192 </A>
Shabana R.
El-Barbary AA.
Yousif NM.
Lawesson S.-O.
Sulfur Lett.
1984,
2:
203
<A NAME="RE09203SS-193">193 </A>
Shabana R.
Boulos LS.
Shaker YM.
Heteroatom Chem.
1999,
10:
25
<A NAME="RE09203SS-194">194 </A>
Nizamov IS.
Al’Metkina LA.
Batyeva VA.
Al’Fonsov VA.
Pudovik AN.
Phosphorus, Sulfur Silicon Relat. Elem.
1992,
72:
229
<A NAME="RE09203SS-195">195 </A>
Nizamov IS.
Popovich AE.
Batyeva ES.
Russ. J. Gen. Chem.
1998,
68:
1972
<A NAME="RE09203SS-196">196 </A>
Nizamov IS.
Sergeenko GG.
Bartyeva ES.
Azancheev NM.
Al’Fonsov VA.
Main Group Chem.
2000,
3:
129
<A NAME="RE09203SS-197">197 </A>
Nizamov IS.
Kuznetzov VA.
Batyeva ES.
Al’Fonsov VA.
Pudovik N.
Heteroatom Chem.
1994,
5:
107
<A NAME="RE09203SS-198">198 </A>
Nizamov IS.
Popovich AE.
Batyeva ES.
Azancheev NM.
Al’Fonsov VA.
Phosphorus, Sulfur Silicon Relat. Elem.
2000,
158:
167
<A NAME="RE09203SS-199">199 </A>
Nizamov IS.
Matseevskii AV.
Bartyeva ES.
Vandyukova II.
Abalonin BE.
Shagidullin RR.
Phosphorus, Sulfur Silicon Relat. Elem.
1997,
126:
137
<A NAME="RE09203SS-200">200 </A>
He L.-N.
Huang T.-B.
Cai F.
Chen R.-Y.
Phosphorus, Sulfur Silicon Relat. Elem.
1998,
132:
147
<A NAME="RE09203SS-201">201 </A>
Sato M.
Asai M.
J. Organomet. Chem.
1992,
430:
105
<A NAME="RE09203SS-202">202 </A>
Beer PD.
Graydon AR.
Johnson AOM.
Smith DK.
Inorg. Chem.
1997,
36:
2112
<A NAME="RE09203SS-203">203 </A>
Imrie C.
Cook L.
Levendis DC.
J. Organomet. Chem.
2001,
637-639:
266
<A NAME="RE09203SS-204">204 </A>
Tárraga A.
Molina P.
Curiel D.
Bautista D.
Tetrahedron: Asymmetry
2002,
13:
1621
<A NAME="RE09203SS-205">205 </A>
Molina P.
Tárraga A.
Curiel D.
Synlett
2002,
435
<A NAME="RE09203SS-206">206 </A>
Kruger GJ.
Lotz S.
Linford L.
van Dyk M.
Raubenheimer HG.
J. Organomet. Chem.
1985,
280:
241
<A NAME="RE09203SS-207">207 </A>
Wood PT.
Woollins JD.
Transition Met. Chem.
1987,
12:
403
<A NAME="RE09203SS-208">208 </A>
Jones R.
Williams DJ.
Wood PT.
Woolins JD.
Polyhedron
1987,
6:
539
<A NAME="RE09203SS-209">209 </A>
Arca M.
Corina A.
Devillanova FA.
Fabretti AC.
Isaia F.
Lippolis V.
Verani G.
Inorg. Chim. Acta
1997,
262:
81
<A NAME="RE09203SS-210">210 </A>
Bigoli F.
Deplano P.
Devillanova FA.
Ferraro JR.
Lippolis V.
Lukes PJ.
Mercuri ML.
Pellinghelli MA.
Trogu EF.
Williams JM.
Inorg. Chem.
1997,
36:
1218
<A NAME="RE09203SS-211">211 </A>
Aragoni MC.
Arca M.
Demartin F.
Devillanova FA.
Garau A.
Isaia F.
Lelj F.
Lippolis V.
Verani G.
J. Am. Chem. Soc.
1999,
121:
7098
<A NAME="RE09203SS-212">212 </A>
Zhao ZR.
Hu X.
Liu ST.
Liu QW.
Chin. Chem. Lett.
1997,
8:
461 ; Chem. Abstr. 1997 , 127 , 103484
<A NAME="RE09203SS-213">213 </A>
Hill AF.
Malget JM.
Chem. Commun.
1996,
1177
<A NAME="RE09203SS-214">214 </A>
Coffey TA.
Hogarth G.
Redmond SP.
Inorg. Chim. Acta
2000,
308:
155
<A NAME="RE09203SS-215">215 </A>
Takaguchi Y.
Furukawa N.
Chem. Lett.
1996,
859
<A NAME="RE09203SS-216">216 </A>
Nizamov IS.
Matseevshii AV.
Batyeva ES.
Azancheev NM.
Vandyukova II.
Shagidullin RR.
Heteroatom Chem.
1999,
10:
399
<A NAME="RE09203SS-217">217 </A>
Nizamov IS.
Kuznetzov V.
Batyeva ES.
Heteroatom Chem.
1997,
8:
323
<A NAME="RE09203SS-218">218 </A>
Carmalt CJ.
Clyburne JAC.
Cowley AH.
Lomeli V.
McBurnett B.
Chem. Commun.
1998,
243
<A NAME="RE09203SS-219">219 </A>
Shimomura N.
Mukaiyama T.
Chem. Lett.
1993,
1941
<A NAME="RE09203SS-220">220 </A>
Shimomura N.
Mukaiyama T.
Bull. Chem. Soc. Jpn.
1994,
67:
2532
<A NAME="RE09203SS-221">221 </A>
Shimomura N.
Matsutani T.
Mukaiyama T.
Bull. Chem. Soc. Jpn.
1994,
67:
3100
<A NAME="RE09203SS-222">222 </A>
Rajagopalan S.
Radke G.
Tomich J.
Synth. Commun.
1997,
27:
187
<A NAME="RE09203SS-223">223 </A>
Eberle MK.
Nuninger F.
Weber H.-P.
J. Org. Chem.
1995,
60:
2610
<A NAME="RE09203SS-224">224 </A>
Nishio T.
J. Chem. Soc., Perkin Trans. 1
1993,
1113
<A NAME="RE09203SS-225">225 </A>
Nishio T.
Chem. Commun.
1989,
205
<A NAME="RE09203SS-226">226 </A>
Tagawa Y.
Minami S.
Yoshida T.
Tanaka K.
Sato S.
Goto Y.
Yamagata K.
Arch. Pharm.
2002,
335:
99
<A NAME="RE09203SS-227">227 </A>
Nishio T.
Okuda N.
Kashima C.
J. Chem. Soc., Perkin Trans. 1
1992,
899
<A NAME="RE09203SS-228">228 </A>
Nishio T.
Okuda N.
Mori Y.
Kashima C.
Synthesis
1989,
396
<A NAME="RE09203SS-229">229 </A>
Rasmussen JB.
Jorgensen KA.
Lawesson S.-O.
Bull. Soc. Chim. Belg.
1978,
87:
307
<A NAME="RE09203SS-230">230 </A>
Tewari N.
Kumar Y.
Thaper RK.
Khanna JM.
Synth. Commun.
1996,
26:
1169
<A NAME="RE09203SS-231">231 </A>
Bartsch H.
Erker T.
Tetrahedron Lett.
1992,
33:
199
<A NAME="RE09203SS-232">232 </A>
Andersson JT.
Kaiser G.
Anal. Chem.
1996,
69:
636
<A NAME="RE09203SS-233">233 </A>
Shimada K.
Kodaki K.
Aoyagi S.
Takikawa Y.
Kabuto C.
Chem. Lett.
1999,
695
<A NAME="RE09203SS-234">234 </A>
Mukaiyama T.
Saito K.
Kitagawa H.
Shimomura N.
Chem. Lett.
1994,
789
<A NAME="RE09203SS-235">235 </A>
Wu C.-Y.
Lin H.-C.
Wang Z.
Wu H.-J.
J. Org. Chem.
2001,
66:
4610
<A NAME="RE09203SS-236">236 </A>
Shimagaki M.
Fujieda Y.
Kimura T.
Nakata T.
Tetrahedron Lett.
1995,
36:
719
<A NAME="RE09203SS-237">237 </A>
Bouancheau C.
Rudler M.
Chelain E.
Rudler H.
Vaissermann J.
Daran J.-C.
J. Organomet. Chem.
1995,
496:
127
<A NAME="RE09203SS-238">238 </A>
Butler RN.
McKenna EC.
Grogan DC.
Chem. Commun.
1997,
2149
<A NAME="RE09203SS-239">239 </A>
Dorn H.
Kreher T.
Heterocycles
1994,
38:
2171
<A NAME="RE09203SS-240">240 </A>
Sharp MJ.
Heathcock CH.
Tetrahedron Lett.
1994,
35:
3651
<A NAME="RE09203SS-241">241 </A>
Thomsen I.
Clausen K.
Scheibye S.
Lawesson S.-O.
Org. Synth.
1984,
62:
158
<A NAME="RE09203SS-242">242 </A>
Nugara PN.
Huang NZ.
Lakshmikantham MV.
Cava MP.
Heterocycles
1991,
32:
1559
<A NAME="RE09203SS-243">243 </A>
Atzrodt J.
Beckert R.
Gunther W.
Gorls H.
Eur. J. Org. Chem.
2000,
1661
<A NAME="RE09203SS-244">244 </A>
Garratt PJ.
Payne D.
Tocher DA.
J. Org. Chem.
1990,
55:
1909
<A NAME="RE09203SS-245">245 </A>
Hadj-Abo F.
Bienz S.
Hesse M.
Tetrahedron
1994,
50:
8665
