Strain-Assisted a-Cleavage Reactions of Thioketones: Cyclobutanethiones

K. Muthuramu; B. Sundari; V. Ramamurthy

doi:10.1021/jo00172a008

Strain-Assisted a-Cleavage Reactions of Thioketones: Cyclobutanethiones

K. Muthuramu, B. Sundari, V. Ramamurthy

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

16 Scopus citations

Abstract

Photochemical α-cleavage from the lowest triplet state (nπ*, T₁), resulting in the generation of a diradical intermediate, appears to be general for cyclobutanethiones. The diradical intermediate derived from 1,3-dithione is observed to undergo ring expansion to carbene or close to either dithione or dithiolactone. The photochemical behavior reported here for cyclobutanethiones is different from that of the corresponding cyclobutanones. α-Cleavage processes in the case of cyclobutanethiones are not efficient and are often accompanied by side reactions.

Original language	English (US)
Pages (from-to)	4482-4487
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	48
Issue number	24
DOIs	https://doi.org/10.1021/jo00172a008
State	Published - Dec 1983
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Strain-Assisted a-Cleavage Reactions of Thioketones: Cyclobutanethiones",

abstract = "Photochemical α-cleavage from the lowest triplet state (nπ*, T1), resulting in the generation of a diradical intermediate, appears to be general for cyclobutanethiones. The diradical intermediate derived from 1,3-dithione is observed to undergo ring expansion to carbene or close to either dithione or dithiolactone. The photochemical behavior reported here for cyclobutanethiones is different from that of the corresponding cyclobutanones. α-Cleavage processes in the case of cyclobutanethiones are not efficient and are often accompanied by side reactions.",

author = "K. Muthuramu and B. Sundari and V. Ramamurthy",

year = "1983",

month = dec,

doi = "10.1021/jo00172a008",

language = "English (US)",

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pages = "4482--4487",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Strain-Assisted a-Cleavage Reactions of Thioketones

T2 - Cyclobutanethiones

AU - Muthuramu, K.

AU - Sundari, B.

AU - Ramamurthy, V.

PY - 1983/12

Y1 - 1983/12

N2 - Photochemical α-cleavage from the lowest triplet state (nπ*, T1), resulting in the generation of a diradical intermediate, appears to be general for cyclobutanethiones. The diradical intermediate derived from 1,3-dithione is observed to undergo ring expansion to carbene or close to either dithione or dithiolactone. The photochemical behavior reported here for cyclobutanethiones is different from that of the corresponding cyclobutanones. α-Cleavage processes in the case of cyclobutanethiones are not efficient and are often accompanied by side reactions.

AB - Photochemical α-cleavage from the lowest triplet state (nπ*, T1), resulting in the generation of a diradical intermediate, appears to be general for cyclobutanethiones. The diradical intermediate derived from 1,3-dithione is observed to undergo ring expansion to carbene or close to either dithione or dithiolactone. The photochemical behavior reported here for cyclobutanethiones is different from that of the corresponding cyclobutanones. α-Cleavage processes in the case of cyclobutanethiones are not efficient and are often accompanied by side reactions.

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