71253-57-1Relevant academic research and scientific papers
Synthesis of α-methylene-β-hydroperoxy sulfoxides by regioselective photooxygenation (Schenck Reaction) of racemic vinyl sulfoxides
Adam,Kumar,Saha-Moller
, p. 1525 - 1528 (2007/10/02)
The β-hydroperoxy vinyl sulfoxides 3 were synthesized in good to excellent yields by regioselective photooxygenation of racemic vinyl sulfoxides 2. Moderate diastereoselectivities were observed in the ene reaction of singlet oxygen (Schenck Reaction) with
A New Syntethic Route to Vinyl Sulfides Utilizing the Reaction of (Phenylthio)carbenes with Nitrile Anions
Harada, Toshiro,Karasawa, Akio,Oku, Akira
, p. 842 - 846 (2007/10/02)
Reactions of nitrile anion (LiCR2R3CN) and (phenylthio)carbenes generated from 1-chloroalkyl phenyl sulfides (R1CH(Cl)SPh) 2a-e by the action of n-BuLi have been shown to be a useful synthetic route to vinyl sulfides (PhSC(R1)=CR2R3) 3a-k (34-91percent).The nucleophilic attack of the nitrile anion on the carbenic species gave the presumed intermediate β-(phenylthio)-β-lithionitrile, which eliminated LiCN to give the expected vinyl sulfides.The application of the present reaction to the synthesis of cyclic vinyl sulfides was successful: the decomposition of the dianion ofω,ω-bis(phenylthio)alkanenitriles (8b, 8c, 11, and 14) affording the corresponding 1-(phenylthio)cycloalkenes (9, 10, 12, and 15) in 12-87percent yields.
