Derivatives of 6β-Methylpenicillanic Acid

John C. Sheehan; Angeliki Buku; Elsamma Chacko; Thomas J. Commons; Young S. Lo; Dagmar R. Ponzi; William C. Schwarzel

doi:10.1021/jo00445a011

Derivatives of 6β-Methylpenicillanic Acid

John C. Sheehan, Angeliki Buku, Elsamma Chacko, Thomas J. Commons, Young S. Lo, Dagmar R. Ponzi, William C. Schwarzel

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Abstract

Diazo compounds 1 have been converted to intermediates 2 by two methods: reaction with aqueous N-bromosuccinimide, and treatment with triphenylphosphine and nitrous acid. Reaction of 2 with Wittig reagents gives a series of C₆ carbon analogues 6 and, after Curtius rearrangement, C₆ penicillin homologues 8.

Original language	English
Pages (from-to)	4045-4048
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	42
Issue number	25
DOIs	https://doi.org/10.1021/jo00445a011
State	Published - 1 Dec 1977
Externally published	Yes

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title = "Derivatives of 6β-Methylpenicillanic Acid",

abstract = "Diazo compounds 1 have been converted to intermediates 2 by two methods: reaction with aqueous N-bromosuccinimide, and treatment with triphenylphosphine and nitrous acid. Reaction of 2 with Wittig reagents gives a series of C6 carbon analogues 6 and, after Curtius rearrangement, C6 penicillin homologues 8.",

author = "Sheehan, {John C.} and Angeliki Buku and Elsamma Chacko and Commons, {Thomas J.} and Lo, {Young S.} and Ponzi, {Dagmar R.} and Schwarzel, {William C.}",

year = "1977",

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T1 - Derivatives of 6β-Methylpenicillanic Acid

AU - Sheehan, John C.

AU - Buku, Angeliki

AU - Chacko, Elsamma

AU - Commons, Thomas J.

AU - Lo, Young S.

AU - Ponzi, Dagmar R.

AU - Schwarzel, William C.

PY - 1977/12/1

Y1 - 1977/12/1

N2 - Diazo compounds 1 have been converted to intermediates 2 by two methods: reaction with aqueous N-bromosuccinimide, and treatment with triphenylphosphine and nitrous acid. Reaction of 2 with Wittig reagents gives a series of C6 carbon analogues 6 and, after Curtius rearrangement, C6 penicillin homologues 8.

AB - Diazo compounds 1 have been converted to intermediates 2 by two methods: reaction with aqueous N-bromosuccinimide, and treatment with triphenylphosphine and nitrous acid. Reaction of 2 with Wittig reagents gives a series of C6 carbon analogues 6 and, after Curtius rearrangement, C6 penicillin homologues 8.

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DO - 10.1021/jo00445a011

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VL - 42

SP - 4045

EP - 4048

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

Derivatives of 6β-Methylpenicillanic Acid

Abstract

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