Photochemistry of α,β-unsaturated thiones: Cycloaddition of thiocoumarin to electron-rich and electron-deficient olefins from T1

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Abstract

Thiocoumarin upon photolysis adds to both electron-rich and -deficient olefins from the lowest triplet state to yield thietane and in some cases 1,4-dithiane. Although the rate of primary interaction between the triplet thiocoumarin and the olefin is high, the quantum yield of the adduct formation is low. A biradical and an exciplex are presumed to be involved as intermediates in the addition process. The observed behavior, although different from that of coumarin, follows largely the general cycloaddition pattern reported thus far for diaryl, dialkyl, and α,β-unsaturated thiones.

Original languageEnglish
Pages (from-to)741-744
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number4
StatePublished - Dec 1 1988
Externally publishedYes

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Thiones
Cycloaddition
Photochemical reactions
Alkenes
Electrons
Photolysis
Quantum yield
coumarin
1,4-dithiane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Thiocoumarin upon photolysis adds to both electron-rich and -deficient olefins from the lowest triplet state to yield thietane and in some cases 1,4-dithiane. Although the rate of primary interaction between the triplet thiocoumarin and the olefin is high, the quantum yield of the adduct formation is low. A biradical and an exciplex are presumed to be involved as intermediates in the addition process. The observed behavior, although different from that of coumarin, follows largely the general cycloaddition pattern reported thus far for diaryl, dialkyl, and α,β-unsaturated thiones.",
author = "S. Devanathan and Vaidhyanathan Ramamurthy",
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T1 - Photochemistry of α,β-unsaturated thiones

T2 - Cycloaddition of thiocoumarin to electron-rich and electron-deficient olefins from T1

AU - Devanathan, S.

AU - Ramamurthy, Vaidhyanathan

PY - 1988/12/1

Y1 - 1988/12/1

N2 - Thiocoumarin upon photolysis adds to both electron-rich and -deficient olefins from the lowest triplet state to yield thietane and in some cases 1,4-dithiane. Although the rate of primary interaction between the triplet thiocoumarin and the olefin is high, the quantum yield of the adduct formation is low. A biradical and an exciplex are presumed to be involved as intermediates in the addition process. The observed behavior, although different from that of coumarin, follows largely the general cycloaddition pattern reported thus far for diaryl, dialkyl, and α,β-unsaturated thiones.

AB - Thiocoumarin upon photolysis adds to both electron-rich and -deficient olefins from the lowest triplet state to yield thietane and in some cases 1,4-dithiane. Although the rate of primary interaction between the triplet thiocoumarin and the olefin is high, the quantum yield of the adduct formation is low. A biradical and an exciplex are presumed to be involved as intermediates in the addition process. The observed behavior, although different from that of coumarin, follows largely the general cycloaddition pattern reported thus far for diaryl, dialkyl, and α,β-unsaturated thiones.

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