Facile syntheses of allylic allenethiosulfinates and -sulfonates, and of beta-iodo alpha,beta-unsaturated gamma-sultines |
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Authors: | Braverman Samuel Pechenick Tatiana Sprecher Milon |
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Institution: | Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. bravers@mail.biu.ac.il |
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Abstract: | The regiospecificity of the 1,4-addition of the recently reported novel alkoxy chlorodisulfides to 2-methyl-1,3-butadiene has been established. Allyl allenethiosulfinates formed by spontaneous 2,3]-sigmatropic rearrangement of the addition products were oxidized at 4 degrees C to the corresponding thiosulfonates. Periodate oxidation at room temperature, preferably in the presence of I2, resulted in oxidative cleavage and cyclization to beta-iodo alpha,beta-unsaturated gamma-sultines. Such sultines, with varying degrees of gamma-alkyl substitution, were also conveniently prepared by reaction of iodine with alkyl allenesulfinates. |
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