Abstract
Reactions of vinylidenecyclopropanes with diaryl diselenide catalyzed by iodosobenzene
diacetate produced the corresponding addition products 4 in moderate to good yields under mild conditions. The further transformation of 4 to the corresponding methylenecyclopropanes 5 has been disclosed in the presence of hydrogen peroxide (H2 O2 ) in toluene.
Key words
arylvinylidenecyclopropanes - diaryl diselenide - iodosobenzene diacetate - methylenecyclopropanes
- addition reaction
References
<A NAME="RU20705ST-1A">1a </A>
Nogueira CW.
Zeni G.
Rocha JBT.
Chem. Rev.
2004,
104:
6255
<A NAME="RU20705ST-1B">1b </A>
Mugesh G.
du Mont WW.
Sies H.
Chem. Rev.
2001,
101:
2125
<A NAME="RU20705ST-1C">1c </A>
Parnham MJ.
Graf E.
Prog. Drug Res.
1991,
36:
9
<A NAME="RU20705ST-1D">1d </A>
Nogueira CW.
Quinhones EB.
Jung EAC.
Zeni G.
Rocha JBT.
Inflammation Res.
2003,
52:
56
<A NAME="RU20705ST-2A">2a </A>
Nicolaou KC.
Petasis NA.
Selenium in Natural Products Synthesis
CIS;
Philadelphia:
1984.
<A NAME="RU20705ST-2B">2b </A>
Paulmier C.
Selenium Reagents and Intermediates in Organic Synthesis
Pergamon;
Oxford:
1986.
<A NAME="RU20705ST-2C">2c </A>
Patai S.
Rappoport Z.
The Chemistry of Organic Selenium and Tellurium Compounds
Vol 1:
Wiley;
New York:
1986.
<A NAME="RU20705ST-2D">2d </A>
Liotta D.
Organoselenium Chemistry
Wiley;
New York:
1987.
<A NAME="RU20705ST-2E">2e </A>
Krief A.
Hevesi L.
Organoselenium Chemistry I
Springer;
Berlin:
1988.
<A NAME="RU20705ST-2F">2f </A>
Back TG.
Organoselenium Chemistry: A Practical Approach
Oxford University Press;
Oxford:
1999.
<A NAME="RU20705ST-2G">2g </A>
Reich HJ.
Acc. Chem. Res.
1979,
12:
22
<A NAME="RU20705ST-2H">2h </A>
Liotta D.
Acc. Chem. Res.
1984,
17:
28
<A NAME="RU20705ST-2I">2i </A>
Wirth T.
Topics in Current Chemistry
Vol. 208:
Springer Verlag;
Heidelberg:
2000.
<A NAME="RU20705ST-2J">2j </A>
Mugesh G.
Singh HB.
Acc. Chem. Res.
2002,
35:
226
<A NAME="RU20705ST-3A">3a </A>
Huguet JL.
Adv. Chem. Ser.
1967,
345
<A NAME="RU20705ST-3B">3b </A>
Sharpless KB.
Young MW.
Lauer RF.
Tetrahedron Lett.
1973,
22:
1979
<A NAME="RU20705ST-4A">4a </A>
Reich HJ.
J. Org. Chem.
1975,
40:
2570
<A NAME="RU20705ST-4B">4b </A>
Sharpless KB.
Lauer RF.
J. Am. Chem. Soc.
1972,
94:
7154
<A NAME="RU20705ST-5">5 </A>
Sevrin M.
Vanende D.
Krief A.
Tetrahedron Lett.
1976,
30:
2643
<A NAME="RU20705ST-6">6 </A>
Sevrin M.
Dumont W.
Hevesi LD.
Krisf A.
Tetrahedron Lett.
1976,
30:
2647
<A NAME="RU20705ST-7A">7a </A>
Seebach D.
Peleties N.
Chem. Ber.
1972,
105:
511
<A NAME="RU20705ST-7B">7b </A>
Seebach D.
Beck AK.
Angew. Chem., Int. Ed. Engl.
1974,
13:
806
<A NAME="RU20705ST-7C">7c </A>
Reich HJ.
Shah SK.
J. Am. Chem. Soc.
1975,
97:
3250
<A NAME="RU20705ST-8">8 </A>
Silveira CC.
Braga AL.
Vieira AS.
Zeni G.
J. Org. Chem.
2003,
68:
662
<A NAME="RU20705ST-9A">9a </A>
Poutsma ML.
Ibarbia PA.
J. Am. Chem. Soc.
1971,
93:
440
<A NAME="RU20705ST-9B">9b </A>
Smadja W.
Chem. Rev.
1983,
83:
263
<A NAME="RU20705ST-9C">9c </A>
Paulson DR.
Crandall JK.
Bunnell CA.
J. Org. Chem.
1970,
35:
3708
<A NAME="RU20705ST-9D">9d </A>
Hendrick ME.
Hardie JA.
Jones M.
J. Org. Chem.
1971,
36:
3061
<A NAME="RU20705ST-9E">9e </A>
Patrick TB.
Haynie EC.
Probst WJ.
J. Org. Chem.
1972,
37:
1553
<A NAME="RU20705ST-9F">9f </A>
Aue DH.
Meshishnek MJ.
J. Am. Chem. Soc.
1977,
99:
223
<A NAME="RU20705ST-9G">9g </A>
Sasaki T.
Eguchi S.
Ogawa T.
J. Am. Chem. Soc.
1975,
97:
4413
<A NAME="RU20705ST-9H">9h </A>
Sadler IH.
Stewart JAG.
J. Chem. Soc., Perkin Trans. 2
1973,
3:
278
<A NAME="RU20705ST-9I">9i </A>
Sugita H.
Mizuno K.
Saito T.
Isagawa K.
Otsuji Y.
Tetrahedron Lett.
1992,
33:
2539
<A NAME="RU20705ST-9J">9j </A>
Mizuno K.
Sugita H.
Kamada T.
Otsuji Y.
Chem. Lett.
1994,
449
<A NAME="RU20705ST-9K">9k </A>
Akasaka T.
Misawa Y.
Ando W.
Tetrahedron Lett.
1990,
31:
1173
<A NAME="RU20705ST-9L">9l </A>
Mizuno K.
Sugita H.
Isagawa K.
Goto M.
Otsuji Y.
Tetrahedron Lett.
1993,
34:
5737
<A NAME="RU20705ST-9M">9m </A>
Mizuno K.
Nire K.
Sugita H.
Otsuji Y.
Tetrahedron Lett.
1993,
34:
6563
<A NAME="RU20705ST-9N">9n </A>
Mizuno K.
Sugita H.
Hirai T.
Maeda H.
Chem. Lett.
2000,
1144
<A NAME="RU20705ST-9O">9o </A>
Mizuno K.
Nire K.
Sugita H.
Maeda H.
Tetrahedron Lett.
2001,
42:
2689
<A NAME="RU20705ST-9P">9p </A>
Mizuno K.
Maeda H.
Sugita H.
Nishioka S.
Hirai T.
Sugimoto A.
Org. Lett.
2001,
3:
581
<A NAME="RU20705ST-9Q">9q </A>
Mizuno K.
Sugita H.
Hirai T.
Maeda H.
Otsuji Y.
Yasuda M.
Hashiguchi M.
Shima K.
Tetrahedron Lett.
2001,
42:
3363
<A NAME="RU20705ST-9R">9r </A>
Maeda H.
Zhen L.
Hirai T.
Mizuno K.
ITE Lett. Batteries, New Technol. Med.
2002,
3:
485
<A NAME="RU20705ST-9S">9s </A>
Sydnes LK.
Chem. Rev.
2003,
103:
1133
For the synthesis of vinylidenecyclopropanes, please see:
<A NAME="RU20705ST-10A">10a </A>
Isagawa K.
Mizuno K.
Sugita H.
Otsuji Y.
J. Chem. Soc., Perkin Trans. 1
1991,
2283 ; and references cited therein
<A NAME="RU20705ST-10B">10b </A>
Sasaki T.
Eguchi S.
Ohno M.
Nakata F.
J. Org. Chem.
1976,
41:
2408
<A NAME="RU20705ST-10C">10c </A>
Sasaki T.
Eguchi S.
Ogawa T.
J. Org. Chem.
1974,
39:
1927
<A NAME="RU20705ST-10D">10d </A>
Sasaki T.
Eguchi S.
Ogawa T.
Heterocycles
1975,
3:
193
<A NAME="RU20705ST-10E">10e </A>
Eguchi S.
Arasaki M.
J. Chem. Soc., Perkin Trans. 1
1988,
1047
<A NAME="RU20705ST-10F">10f </A>
Sugita H.
Mizuno K.
Mori T.
Isagawa K.
Otsuji Y.
Angew. Chem., Int. Ed. Engl.
1991,
30:
984
<A NAME="RU20705ST-10G">10g </A>
Patrick TB.
Tetrahedron Lett.
1974,
15:
1407
<A NAME="RU20705ST-10H">10h </A>
Al-Dulayymi JR.
Baird MS.
J. Chem. Soc., Perkin Trans. 1
1994,
1547
<A NAME="RU20705ST-10I">10i </A>
Patrick TB.
Schmidt DJ.
J. Org. Chem.
1977,
42:
3354
<A NAME="RU20705ST-10J">10j </A>
Hartzler HD.
J. Am. Chem. Soc.
1971,
93:
4527
The other papers related to vinylidenecyclopropanes. See for the reactions of vinylidenecyclopropanes
with carbenes and carbene complexes:
<A NAME="RU20705ST-11A">11a </A>
Crandall JK.
Paulson DR.
Bunnell CA.
Tetrahedron Lett.
1969,
48:
4217
<A NAME="RU20705ST-11B">11b </A>
Hwu C.-C.
Wang F.-C.
Yeh M.-CP.
J. Organomet. Chem.
1994,
474:
123
<A NAME="RU20705ST-11C">11c </A>
Billups WE.
Haley MM.
Boese R.
Blaser D.
Tetrahedron
1994,
50:
10693
<A NAME="RU20705ST-11D">11d </A>
Maeda H.
Hirai T.
Sugimoto A.
Mizuno K.
J. Org. Chem.
2003,
68:
7700
<A NAME="RU20705ST-11E">11e </A>
Bloch R.
Perchec PL.
Conia J.-M.
Angew. Chem., Int. Ed. Engl.
1970,
9:
798
<A NAME="RU20705ST-11F">11f </A>
Pasto DJ.
Yang SH.
J. Org. Chem.
1986,
51:
1676
For the addition reactions to vinylidenecyclopropanes:
<A NAME="RU20705ST-11G">11g </A>
Pasto DJ.
Miles MF.
J. Org. Chem.
1976,
41:
2068
<A NAME="RU20705ST-11H">11h </A>
Pasto DJ.
Chen AF.-T.
Binsch G.
J. Am. Chem. Soc.
1973,
95:
1553
<A NAME="RU20705ST-11I">11i </A>
Pasto DJ.
Chen A.
J. Am. Chem. Soc.
1971,
93:
2562
<A NAME="RU20705ST-11J">11j </A>
Pasto DJ.
Borchardt JK.
Fehlner TP.
Baney HF.
Schwartz ME.
J. Am. Chem. Soc.
1976,
98:
526
<A NAME="RU20705ST-11K">11k </A>
Pasto DJ.
Fehlner TP.
Schwartz ME.
Baney HF.
J. Am. Chem. Soc.
1976,
98:
530
<A NAME="RU20705ST-11L">11l </A>
Pasto DJ.
Miles MF.
J. Org. Chem.
1976,
41:
425
<A NAME="RU20705ST-11M">11m </A>
Pasto DJ.
Chen AF.-T.
Cuirdaru G.
Paquette LA.
J. Org. Chem.
1973,
38:
1015
<A NAME="RU20705ST-11N">11n </A>
Gompper R.
Lach D.
Tetrahedron Lett.
1973,
29:
2683
<A NAME="RU20705ST-11O">11o </A>
Poutsma ML.
Ibarbia PA.
J. Am. Chem. Soc.
1971,
93:
440
<A NAME="RU20705ST-11P">11p </A>
Gompper R.
Lach D.
Tetrahedron Lett.
1973,
29:
2687
<A NAME="RU20705ST-11Q">11q </A>
Pasto DJ.
Wampfler D.
Tetrahedron Lett.
1974,
22:
1933
<A NAME="RU20705ST-11R">11r </A>
Sasaki T.
Eguchi S.
Ogawa T.
J. Am. Chem. Soc.
1975,
97:
4413
<A NAME="RU20705ST-11S">11s </A>
Pasto DJ.
Whitmer JL.
J. Org. Chem.
1980,
45:
1987
<A NAME="RU20705ST-11T">11t </A>
Pasto DJ.
Brophy JE.
J. Org. Chem.
1991,
56:
4554
<A NAME="RU20705ST-11U">11u </A>
Cairns PM.
Combie L.
Pattenden G.
Tetrahedron Lett.
1982,
23:
1405
<A NAME="RU20705ST-11V">11v </A>
Crombie L.
Maddocks PJ.
Pattenden G.
Tetrahedron Lett.
1978,
19:
3483
<A NAME="RU20705ST-12">12 </A>
Shi M.
Wang B.-Y.
Li J.
Eur. J. Org. Chem.
2005,
759
It has been reported that treatment of diphenyl diselenide with iodosobenzene diacetate
produces an electrophilic selenenylating agent for double bonds. See:
<A NAME="RU20705ST-13A">13a </A>
Tingoli M.
Tiecco M.
Testaferri L.
Temperini A.
Synth. Commun.
1998,
28:
1769
<A NAME="RU20705ST-13B">13b </A>
Tiecco M.
Tingoli M.
Testaferri L.
Pure Appl. Chem.
1993,
65:
715 ; and references cited therein
<A NAME="RU20705ST-13C">13c </A>
Miyoshi N.
Takai Y.
Murai S.
Sonoda N.
Bull. Chem. Soc. Jpn.
1978,
51:
1265
<A NAME="RU20705ST-13D">13d </A>
Brugier D.
Outurquin F.
Paulmier C.
J. Chem. Soc., Perkin Trans. 1
2001,
37
<A NAME="RU20705ST-14">14 </A>
The crystal data of 4a has been deposited in CCDC with number 249984. Empirical formula: C35 H28 Se2 ; formula weight: 606.49; crystal color, habit: colourless, prismatic; crystal system:
triclinic; lattice type: primitive; lattice parameters: a = 10.0837 (10) Å, b = 10.8046 (11) Å, c = 13.6399 (14) Å, α = 72.303 (2)°, β = 82.804 (2)°, γ = 84.953 (2)°, V = 1402.6 (2)Å3 ; space group: P-1; Z = 2; D
calc
= 1.436 g/cm3 ; F
000 = 612; diffractometer: Rigaku AFC7R; residuals: R; Rw : 0.0529, 0.1240.
<A NAME="RU20705ST-15">15 </A>
Chen D.-W.
Chen Z.-C.
Tetrahedron Lett.
1994,
41:
7637
<A NAME="RU20705ST-16A">16a </A>
Siehl H.-U.
Aue DH.
Dicoordinated Carbocations
Rappoport Z.
Stang PJ.
John Wiley and Sons;
New York:
1997.
p.137-138
The stabilizing effect of cyclopropyl substituents in carbocations is well documented.
See:
<A NAME="RU20705ST-16B">16b </A>
Olah GA.
Reddy VP.
Prakash GKS.
Chem. Rev.
1992,
92:
69
<A NAME="RU20705ST-16C">16c </A>
Carey FA.
Sundberg RJ.
Advanced Organic Chemistry
5th ed.:
Plenum Press;
New York:
1998.
p.221
<A NAME="RU20705ST-16D">16d </A>
Carey FA.
Sundberg RJ.
Advanced Organic Chemistry
5th ed.:
Plenum Press;
New York:
1998.
p.419
<A NAME="RU20705ST-16E">16e </A>
Carey FA.
Tremper HS.
J. Am. Chem. Soc.
1969,
91:
2967
<A NAME="RU20705ST-17A">17a </A>
Halazy S.
Krief A.
Tetrahedron Lett.
1981,
22:
2135
<A NAME="RU20705ST-17B">17b </A>
Liu L.-P.
Shi M.
Chem. Commun.
2004,
2878
For reviews, see:
<A NAME="RU20705ST-18A">18a </A>
Reich HJ.
Wollowitz S.
Org. React.
1993,
44:
1
<A NAME="RU20705ST-18B">18b </A>
Back TG.
Organoselenium Chemistry
Back TG.
Oxford University Press;
Oxford:
1999.
p.7-33
<A NAME="RU20705ST-18C">18c </A>
Nishibayash Y.
Uemura S.
Top. Curr. Chem.
2000,
208:
201
<A NAME="RU20705ST-19">19 </A> For a review, see:
Reich HJ.
Organoselenium Chemistry
Liotta D.
Jossey-Bass;
New York:
1987.
p.365-394
<A NAME="RU20705ST-20">20 </A>
General Procedure.
Under an argon atmosphere, vinylidenecyclopropanes (0.3 mmol), diphenyl diselenide (0.6 mmol), PhI(OAc)2 (0.1 mmol), and THF (2 mL) were added into a Schlenk tube. The mixture was stirred
at 35-40 °C for the time specified in Table
[2 ]
, then was purified by a flash column chromatography.