REARRANGEMENT MECHANISMS OF SOME CYCLIC SULFOXIDES

WS Lee, K Lee, KD Nam

Index: Lee, Wha Suk; Lee, Koo; Nam, Kee Dal Phosphorus, Sulfur and Silicon and the Related Elements, 1991 , vol. 59, # 1-4 p. 189 - 192

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Abstract

Abstract Under neutral conditions cis sulfoxides 5 underwent a sigmatropic rearrangement with 2-methylene hydrogens to give sulfenic acids 18, followed by Cyclization to dihydro-1, 4- dithiins 2. The trans sulfoxides 6 rearranged involving 2-methyl hydrogens to form isomeric dihydrodithiins 3 via sulfenic acids 19. In the reactions of both the sulfoxides, sulfides 4 and disulfides 11 were also formed as minor side products. In the presence of acid catalyst cis ...