Russian Chemical Bulletin p. 1846 - 1852 (2000)
Update date:2022-08-05
Topics:
Zyk, N. V.
Beloglazkina, E. K.
Below, M. A.
Zefirov, N. S.
The reactions of alkynes with arylsulfenamides activated with phosphorus oxohalides giving rise to aryl β-halovinyl sulfides were investigated. The reactions with acetylene, oct-1-yne, and oct-4-yne are trans-stereospecific, whereas the reaction with phenylacetylene afforded a mixture of cis- and trans-addition products. The addition to unsymmetrical alkynes yielded a mixture of Markovnikoff and anti-Markovnikoff isomers whose ratio depends on the solvent. Products of addition to oct-1-yne in the presence of catalytic amounts of acids underwent isomerization.
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