The Journal of Organic Chemistry

Structure and stereochemistry of phospholene sulfides from reaction of hydrogen sulfide with diene-phosphonous dihalide cycloadducts

C Symmes Jr, LD Quin

Index: Symmes,C.; Quin,L.D. Journal of Organic Chemistry, 1976 , vol. 41, # 9 p. 1548 - 1551

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Citation Number: 10

Abstract

The cycloadduct (a I-halophospholenium halide) from butadiene and methylphosphonous dichloride reacts smoothly with hydrogen sulfide to form I-methyl-3-phospholene sulfide, rearrangeable with base (in part) or acid (complete) to the isomeric 2-phospholene sulfide. The chloroprene cycloadduct treated with H2S gave exclusively the 2-phospholene sulfide; the chlorine was replaceable by methoxide ion to form the enol ether, which was easily ...