Photochemical transformations. Part 36. Synthesis and photolytic ring contraction of mesoionic 2-Alkylthiothiazol-4-ones; a new route to β-lactams

Derek H.R. Barton; Ernst Buschmann; Johannes Hausler; Cedric W. Holzapfel; Tuvia Sheradsky; Derryck A. Taylor

doi:10.1039/p19770001107

Photochemical transformations. Part 36. Synthesis and photolytic ring contraction of mesoionic 2-Alkylthiothiazol-4-ones; a new route to β-lactams

Derek H.R. Barton
, Ernst Buschmann
, Johannes Hausler
, Cedric W. Holzapfel
, Tuvia Sheradsky
, Derryck A. Taylor

Imperial College London

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

A number of mesoionic 2-alkylthiothiazol-4-ones (6) were prepared by alkylation of rhodanines or by the reaction of α-bromomalonates with dithiocarbamates. The photolysis of these mesoionic compounds proceeds via a highly strained, bicyclic, ring contraction product which rearranges to a thiazolin-2-one (14), loses sulphur, affording a β-aminoacrylate (11), or is trapped by methanol giving methoxy-β-lactams (12) and (13).

Original language	English
Pages (from-to)	1107-1114
Number of pages	8
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	9
DOIs	https://doi.org/10.1039/p19770001107
Publication status	Published - 1977
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1039/p19770001107

Cite this

@article{c071b66503c44ae9a2907c1652cfb418,

title = "Photochemical transformations. Part 36. Synthesis and photolytic ring contraction of mesoionic 2-Alkylthiothiazol-4-ones; a new route to β-lactams",

abstract = "A number of mesoionic 2-alkylthiothiazol-4-ones (6) were prepared by alkylation of rhodanines or by the reaction of α-bromomalonates with dithiocarbamates. The photolysis of these mesoionic compounds proceeds via a highly strained, bicyclic, ring contraction product which rearranges to a thiazolin-2-one (14), loses sulphur, affording a β-aminoacrylate (11), or is trapped by methanol giving methoxy-β-lactams (12) and (13).",

author = "Barton, \{Derek H.R.\} and Ernst Buschmann and Johannes Hausler and Holzapfel, \{Cedric W.\} and Tuvia Sheradsky and Taylor, \{Derryck A.\}",

year = "1977",

doi = "10.1039/p19770001107",

language = "English",

pages = "1107--1114",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Royal Society of Chemistry",

number = "9",

}

TY - JOUR

T1 - Photochemical transformations. Part 36. Synthesis and photolytic ring contraction of mesoionic 2-Alkylthiothiazol-4-ones; a new route to β-lactams

AU - Barton, Derek H.R.

AU - Buschmann, Ernst

AU - Hausler, Johannes

AU - Holzapfel, Cedric W.

AU - Sheradsky, Tuvia

AU - Taylor, Derryck A.

PY - 1977

Y1 - 1977

N2 - A number of mesoionic 2-alkylthiothiazol-4-ones (6) were prepared by alkylation of rhodanines or by the reaction of α-bromomalonates with dithiocarbamates. The photolysis of these mesoionic compounds proceeds via a highly strained, bicyclic, ring contraction product which rearranges to a thiazolin-2-one (14), loses sulphur, affording a β-aminoacrylate (11), or is trapped by methanol giving methoxy-β-lactams (12) and (13).

AB - A number of mesoionic 2-alkylthiothiazol-4-ones (6) were prepared by alkylation of rhodanines or by the reaction of α-bromomalonates with dithiocarbamates. The photolysis of these mesoionic compounds proceeds via a highly strained, bicyclic, ring contraction product which rearranges to a thiazolin-2-one (14), loses sulphur, affording a β-aminoacrylate (11), or is trapped by methanol giving methoxy-β-lactams (12) and (13).

UR - https://www.scopus.com/pages/publications/37049092535

U2 - 10.1039/p19770001107

DO - 10.1039/p19770001107

M3 - Article

AN - SCOPUS:37049092535

SN - 1472-7781

SP - 1107

EP - 1114

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 9

ER -

Photochemical transformations. Part 36. Synthesis and photolytic ring contraction of mesoionic 2-Alkylthiothiazol-4-ones; a new route to β-lactams

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this