Sulfinyl halides and their preparation from penicillin sulfoxide

Details Sulfinyl halides and their preparation from penicillin sulfoxide Sulfinyl halides and their preparation from penicillin sulfoxide

1976-04-02

1978-03-28

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

560 30, 560 22, 260307H, 260326S, 2603265FM, 2603322H, 560161, 560115, 560136, 560137, 260553A, 260553R, 260556R, 260556A, 544 18, 544 22, 548311, 548318, C07D20508, C07D40306, C07D40906, C07D41306

Patent

active

040814408

ABSTRACT:
A penicillin sulfoxide ester is reacted with an N-chloro halogenating agent at a temperature of from about 75.degree. C. to about 135.degree. C. to produce a novel 2-chlorosulfinylazetidin-4-one intermediate. The intermediate can be treated with stannic chloride to produce a 3-exomethylenecepham sulfoxide.

REFERENCES:
patent: 3843682 (1974-10-01), Kukolja et al.
patent: 3852281 (1974-12-01), Verweij
patent: 3852282 (1974-12-01), Dolfini
patent: 3864338 (1975-02-01), Bohme et al.
patent: 4009159 (1977-02-01), Kamiya et al.
Kukolja et al., Ang. Chem. Int. Ed., vol. 12, pp. 67-68 (1973).
Chou et al., J. Am Chem. Soc., vol. 96, pp. 1609-1610 (1974).
Cooper et al., J. Am. Chem. Soc., vol. 92, pp. 2575-2576 (1970).
Huff et al., Chem. Abstracts, vol. 80, Abstract No. 95380n (1974).
Barton et al., Chem. Comm., 1971, pp. 1137-1139.
Stirling, Int. J. Sulfur Chem., B, vol. 6, pp. 296, 297, 285 (1971).
Tuleen et al., Chemistry and Industry, 1966, pp. 1555-1556.
Kukolja et al., J. Am. Chem. Soc., vol. 94, pp. 7169-7170 (1972).

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