Tetrahedron

Photochemical ring closure of α, α-bisulfenylated carbonyl compounds: Stereoselective formation of cix-dihydrobenzothiophenes

T Sasaki, K Hayakawa, S Nishida

Index: Sasaki, Tadashi; Hayakawa, Kenji; Nishida, Sumio Tetrahedron, 1982 , vol. 38, # 1 p. 75 - 83

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Citation Number: 9

Abstract

Photochemistry of α, α-bisulfenylated ketone has been investigated. Irradiation of 2- phenylthiodihydrothiophen-3-one (1) in benzene gave the radical recombination products 9 (63%) and 10 (49%). In a polar solvent, the ionic chemistry became predominant. Brief irradiation of 1 in acetonitrile and methanol gave the cis-fused dihydrothiophene 11 as the major product in 43% and 20% yields, respectively. The stereoselective photocyclization ...