57991-97-6Relevant articles and documents
Reactions of sulfenamides with alkynes in the presence of phosphorus(V) oxohalides
Zyk, N. V.,Beloglazkina, E. K.,Below, M. A.,Zefirov, N. S.
, p. 1846 - 1852 (2007/10/03)
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.