TY - JOUR
T1 - Photochemistry of α,β-Unsaturated Thiones
T2 - Addition to Electron-Rich Olefins from T1
AU - Pushkara Rao, V.
AU - Ramamurthy, V.
PY - 1988/1/1
Y1 - 1988/1/1
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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U2 - 10.1021/jo00237a020
DO - 10.1021/jo00237a020
M3 - Article
AN - SCOPUS:0040050030
VL - 53
SP - 327
EP - 332
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 2
ER -