Abstract
1,1,3-Trimethyl-2-thioxo-l,2-dihydronaphthalene (1) adds to electron-rich olefins upon excitation to either S2 (ππ*) or S1 (nπ*) states. Excitation to S2 level resulted in the same mixture of products, namely thietane and 1,4-dithiane, as on excitation to S1 level. Addition occurs to the thiocarbonyl function and not to the carbon-carbon double bond. The addition is site-specific, and the formation of thietane is regiospecific. The ratio of thietane to 1,4-dithiane in the product mixture is dependent on the concentration of the thioenone. The addition is suggested to originate from the lowest triplet state (T1) and involves diradical intermediates.
| Original language | English |
|---|---|
| Pages (from-to) | 327-332 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 53 |
| Issue number | 2 |
| State | Published - Dec 1 1988 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Photochemistry of α,β-unsaturated thiones : Addition to electron-rich olefins from T1. / Pushkara Rao, V.; Ramamurthy, Vaidhyanathan.
In: Journal of Organic Chemistry, Vol. 53, No. 2, 01.12.1988, p. 327-332.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Photochemistry of α,β-unsaturated thiones
T2 - Addition to electron-rich olefins from T1
AU - Pushkara Rao, V.
AU - Ramamurthy, Vaidhyanathan
PY - 1988/12/1
Y1 - 1988/12/1
N2 - 1,1,3-Trimethyl-2-thioxo-l,2-dihydronaphthalene (1) adds to electron-rich olefins upon excitation to either S2 (ππ*) or S1 (nπ*) states. Excitation to S2 level resulted in the same mixture of products, namely thietane and 1,4-dithiane, as on excitation to S1 level. Addition occurs to the thiocarbonyl function and not to the carbon-carbon double bond. The addition is site-specific, and the formation of thietane is regiospecific. The ratio of thietane to 1,4-dithiane in the product mixture is dependent on the concentration of the thioenone. The addition is suggested to originate from the lowest triplet state (T1) and involves diradical intermediates.
AB - 1,1,3-Trimethyl-2-thioxo-l,2-dihydronaphthalene (1) adds to electron-rich olefins upon excitation to either S2 (ππ*) or S1 (nπ*) states. Excitation to S2 level resulted in the same mixture of products, namely thietane and 1,4-dithiane, as on excitation to S1 level. Addition occurs to the thiocarbonyl function and not to the carbon-carbon double bond. The addition is site-specific, and the formation of thietane is regiospecific. The ratio of thietane to 1,4-dithiane in the product mixture is dependent on the concentration of the thioenone. The addition is suggested to originate from the lowest triplet state (T1) and involves diradical intermediates.
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M3 - Article
VL - 53
SP - 327
EP - 332
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 2
ER -