Chlorination of Oximes with Aqueous H2O2/HCl System: Facile Synthesis of gem-Chloronitroso- and gem-Chloronitroalkanes, gem-Chloronitroso- and gem-Chloronitrocycloalkanes

Alexander O. Terent’ev; Igor B. Krylov; Yuri N. Ogibin; Gennady I. Nikishin

doi:10.1055/s-2006-950304

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Synthesis 2006(22): 3819-3824
DOI: 10.1055/s-2006-950304

PAPER

Chlorination of Oximes with Aqueous H₂O₂/HCl System: Facile Synthesis of gem-Chloronitroso- and gem-Chloronitroalkanes, gem-Chloronitroso- and gem-Chloronitrocycloalkanes

Alexander O. Terent’ev*, Igor B. Krylov, Yuri N. Ogibin, Gennady I. Nikishin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia
Fax: +7(495)1355328; e-Mail: terentev@ioc.ac.ru;

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Publication History

Received 5 June 2006
Publication Date:
09 October 2006 (online)

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Abstract

Chlorination of cyclic and linear ketone oximes with aqueous H₂O₂/HCl in a two-phase dichloromethane-water system selectively affords gem-chloronitroso compounds in yields of up to 94%. One-pot oxidation of the resulting gem-chloronitroso compounds with peracetic acid, prepared in situ, gives gem-chloronitroalkanes and cycloalkanes in yields of up to 82%. The advantages of the method are that it is facile and environmentally benign and does not require gaseous chlorine.

Key words

oximes - gem-chloronitroso compounds - gem-chloronitro compounds - chlorination - oxidation - hydrogen peroxide

References

1 Barhate NB. Gajare AS. Wakharkar RD. Bedekar AV. Tetrahedron 1999, 55: 11127

Crossref Google Scholar
2 Barhate NB. Gajare AS. Wakharkar RD. Bedekar AV. Tetrahedron Lett. 1998, 39: 6349

Crossref Google Scholar
3 Bora U. Bose G. Chaudhuri MK. Dhar SS. Gopinath R. Khan AT. Patel BK. Org. Lett. 2000, 2: 247

Crossref Google Scholar
4 Terent’ev AO. Khodykin SV. Troitskii NA. Ogibin YuN. Nikishin GI. Synthesis 2004, 2845

Article in Thieme Connect Google Scholar
5 Terent’ev AO. Khodykin SV. Krylov IB. Ogibin YuN. Nikishin GI. Synthesis 2006, 1087

Article in Thieme Connect Google Scholar
6 Arutyunyan VS. Kochikyan TV. Egiazaryan NS. Avetisyan AA. Russ. J. Org. Chem. 1995, 31: 90 ; Zh. Org. Khim. 1995, 31, 100

Google Scholar
7 Rudakova NI. Anufrieva OV. Smirnova EA. J. Gen. Chem. USSR (Engl. Transl.) 1992, 62: 1887 : Zh. Obshch. Khim. 1992, 62, 2290

Google Scholar
8 Rudakova NI. Erykalov YuG. Zharikova SM. Dmitrieva EV. Mataradze MS. Russ. J. Gen. Chem. 1995, 65: 271 ; Zh. Obshch. Khim. 1995, 65, 315

Google Scholar
9 Dakka J. Sasson Y. J. Chem. Soc., Chem. Commun. 1987, 1421

Crossref Google Scholar
10 Bhatkhande BS. Adhikari MV. Samant SD. Ultrason. Sonochem. 2002, 9: 31

Crossref Google Scholar
11 Vyas PV. Bhatt AK. Ramachandraiah G. Bedekar AV. Tetrahedron Lett. 2003, 44: 4085

Crossref Google Scholar
12 Bezodis P. Hanson JR. Petit P. J. Chem. Res., Synop. 1996, 334

Google Scholar
13 Andrievskii AM. Gorelik MV. Avidon SV. Al’tman ESh. Russ. J. Org. Chem. 1993, 29: 1519 ; Zh. Org. Khim. 1993, 29, 1828

Google Scholar
14 Hanson JR. Opakunle A. Petit P. J. Chem. Res., Synop. 1995, 457

Google Scholar
15 Tillu VH. Shinde PD. Bedekar AV. Wakharkar RD. Synth. Commun. 2003, 33: 1399

Crossref Google Scholar
16a Mukhopadhyay S. Ananthakrishnan S. Chandalia SB. Org. Process Res. Dev. 1999, 3: 10

Crossref Google Scholar
16b Mukhopadhyay S. Ananthakrishnan S. Chandalia SB. Org. Process Res. Dev. 1999, 3: 196

Crossref Google Scholar
16c Mukhopadhyay S. Ananthakrishnan S. Chandalia SB. Org. Process Res. Dev. 1999, 3: 451

Crossref Google Scholar
17 Espenson JH. Zhu Z. Zauche TH. J. Org. Chem. 1999, 64: 1191

Crossref Google Scholar
18 Sharma VB. Jain SL. Sain B. Synlett 2005, 173

Article in Thieme Connect Google Scholar
19 Taylor R. Electrophilic Aromatic Substitution Wiley; New York: 1990.

Google Scholar
20 Corey EJ. Estreicher H. Tetrahedron Lett. 1980, 21: 1117

Crossref Google Scholar
21 Sakai I. Kawabe N. Ohno M. Bull. Chem. Soc. Jpn. 1979, 52: 3381

Crossref Google Scholar
22 Tordeux M. Boumizane K. Wakselman C. J. Fluorine Chem. 1995, 70: 207

Crossref Google Scholar
23 Archibald TG. Baum K. J. Org. Chem. 1988, 53: 4645

Crossref Google Scholar
24 Arbuzov YuA. Markowskaja A. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1952, 355 ; Izv. Akad. Nauk SSSR Ser. Khim. 1952, 363

Crossref Google Scholar
25 Belleau B. Au-Young Y.-K. J. Am. Chem. Soc. 1963, 85: 64

Crossref Google Scholar
26 Arbuzov YuA. Onishchenko AA. Dokl. Chem. (Engl. Transl.) 1962, 146: 875 ; Dokl. Akad. Nauk SSSR, 1962, 146, 1075

Google Scholar
27 Iida H. Watanabe Y. Kibayashi C. J. Org. Chem. 1985, 50: 1818

Crossref Google Scholar
28 Nelsen SF. Thompson-Colon JA. Kirste B. Rosenhouse A. Kaftory M. J. Am. Chem. Soc. 1987, 109: 7128

Crossref Google Scholar
29 Kresze G. Kysela E. Dittel W. Liebigs Ann. Chem. 1981, 210

Google Scholar
30 Werbitzky O. Klier K. Felber H. Liebigs Ann. Chem. 1990, 267

Google Scholar
31 Kresze G. Dittel W. Liebigs Ann. Chem. 1981, 610

Google Scholar
32 Schuerrle K. Beier B. Piepersberg W. J. Chem. Soc., Perkin Trans. 1 1991, 2407

Crossref Google Scholar
33 Iida H. Watanabe Y. Kibayashi C. Tetrahedron Lett. 1984, 44: 5091

Google Scholar
34 Shi G.-Q. Schlosser M. Tetrahedron 1993, 49: 1445

Crossref Google Scholar
35 Ranganathan D. Ranganathan S. Rao CB. Raman K. Tetrahedron 1981, 37: 629

Crossref Google Scholar
36 Defoin A. Joubert M. Heuchel J.-M. Strehler C. Streith J. Synthesis 2000, 1719

Article in Thieme Connect Google Scholar
37 Filip SV. Sewald N. Synthesis 2005, 3565

Article in Thieme Connect Google Scholar
38 Morris AD. Frinault T. Benhida R. Gharbaoui T. Lechevallier A. Beugelmans R. Bull. Soc. Chim. Fr. 1995, 132: 178

Google Scholar
39 Archibald TG. Garver LG. Baum K. Cohen MC. J. Org. Chem. 1989, 54: 2869

Crossref Google Scholar
40 Ono N. Tamura R. Hayami J.-i. Kaji A. Chem. Lett. 1977, 189

Crossref Google Scholar
41 Russell GA. Mudryk B. Jawdosiuk M. Synthesis 1981, 62

Article in Thieme Connect Google Scholar
42 Ono N. Tamura R. Eto H. Hamamoto I. Nakatsuka T. J. Org. Chem. 1983, 48: 3678

Crossref Google Scholar
43 Russell GA. Hershberger J. J. Chem. Soc., Chem. Commun. 1980, 216

Crossref Google Scholar
44 Müller E. Fries D. Metzger H. Chem. Ber. 1955, 88: 1891

Crossref Google Scholar
45 Mackor A. de Boer ThJ. Recl. Trav. Chim. Pays-Bas 1970, 89: 151

Google Scholar
46 Wichterle O. Hudlicky M. Collect. Czech. Chem. Commun. 1947, 12: 661

Crossref Google Scholar
47 Hammick DL. Lister MW. J. Chem. Soc. 1937, 489

Google Scholar
48 Kumar V. Kaushik MP. Tetrahedron Lett. 2005, 46: 8121

Crossref Google Scholar
49 Barnes MW. Patterson JM. J. Org. Chem. 1976, 41: 733

Crossref Google Scholar
50 Ceccherelli P. Curini M. Epifano F. Marcotullio MC. Rosati O. Tetrahedron Lett. 1998, 39: 4385

Crossref Google Scholar
51 Walters TR. Zajac WW. Woods JM. J. Org. Chem. 1991, 56: 316

Crossref Google Scholar
52 Zaks A. Yabannavar AV. Dodds DR. Evans CA. Das PR. Malchow R. J. Org. Chem. 1996, 61: 8692

Crossref Google Scholar
53 Moiseev IK. Mratkhuzina TA. Makarova NV. Russ. J. Gen. Chem. 1999, 69: 1777 ; Zh. Obshch. Khim. 1999, 69, 1855

Google Scholar
54 Makosza M. Kwast A. Kwast E. Jonczyk A. J. Org. Chem. 1985, 50: 3722

Crossref Google Scholar
55 Amrollah-Madjdabadi A. Beugelmans R. Lechevallier A. Synthesis 1986, 826

Article in Thieme Connect Google Scholar
56 Barber GN. Olofson RA. J. Org. Chem. 1978, 43: 3015

Crossref Google Scholar
57 Johnston TP. McCaleb GS. Opliger PS. Laster WR. Montgomery JA. J. Med. Chem. 1971, 14: 600

Crossref Google Scholar
58 Simunic-Meznaric V. Mihalic Z. Vancik H. J. Chem. Soc., Perkin Trans. 2 2002, 2154

Crossref Google Scholar
59 Ruzicka L. Kobelt M. Häfliger O. Prelog V. Helv. Chim. Acta 1949, 32: 544

Crossref Google Scholar
60 Sacharkin LI. Shigarewa GG. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1962, 168 ; Izv. Akad. Nauk SSSR Ser. Khim. 1962, 183

Crossref Google Scholar
61 Adamopoulos S. Boulton AJ. Tadayoni R. Webb GA. J. Chem. Soc., Perkin Trans. 1 1987, 2073

Crossref Google Scholar
62 Wilcox M, and Taylor JB. inventors; (Ciba-Geigy A.-G.) Ger. Offen. 2338010. Chem. Abstr. 1974, 80, 132803
63 von Braun J. Kröper H. Chem. Ber. 1929, 62: 2883

Google Scholar
64 Battiste DR. Traynham JG. J. Org. Chem. 1975, 40: 1239

Crossref Google Scholar
65 Kosinski M. Soc. Sci. Lodz. Acta Chim. 1964, 9: 93

Google Scholar
66 Dieckmann H. Luettke W. Chem. Ber. 1972, 105: 1899

Crossref Google Scholar
67 Funabashi M. Tanaka A. Anselme JP. Bull. Chem. Soc. Jpn. 1972, 45: 2958

Crossref Google Scholar
68 Curini M. Epifano F. Marcotullio MC. Rosati O. Rossi M. Tetrahedron 1999, 55: 6211

Crossref Google Scholar