Facile syntheses of allylic allenethiosulfinates and -sulfonates, and of beta-iodo alpha,beta-unsaturated gamma-sultines.
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.
Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. bravers@mail.biu.ac.il
Samuel
S
Braverman
Tatiana
T
Pechenick
Milon
M
Sprecher
D000498:Allyl Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000138:chemical synthesis*; D013451:Sulfonic Acids / Q000138:chemical synthesis*
D000498:Allyl Compounds; D013441:Sulfinic Acids; D013451:Sulfonic Acids