Tetrahedron letters

Effect of remote heteroatom substituents on stereochemistry in 1, 2 h migration to divalent carbon. Evidence for “negative” hyperconjugation of carbene lone pair

H Tomioka, N Hayashi, N Inoue, Y Izawa

Index: Tomioka, Hideo; Hayashi, Norihiro; Inoue, Noboru; Izawa, Yasuji Tetrahedron Letters, 1985 , vol. 26, # 13 p. 1651 - 1654

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Citation Number: 9

Abstract

Abstract Aryloxymethylchlorocarbene generated by photolysis of the corresponding diazirine afforded α-aryloxy-β-chloroalkene. The thermodynamically less stable Z-products are the major isomers and its content becomes dominant as more electron-withdrawing groups are introduced on phenyl ring.