169612-87-7Relevant academic research and scientific papers
Acid-promoted C1-C2 Bond Fission and Subsequent 1,5-Sulfenyl Shift of 1-Acceptor-1-sulfenyl-substituted 2-Vinylcyclopropanes. Formation of 6-Sulfenyl-α,β-γ,δ-unsaturated Carboxylic Esters and Nitriles
Kataoka, Tadashi,Matsumoto, Harutoshi,Iwama, Tetsuo,Shimizu, Hiroshi
, p. 459 - 460 (1995)
1-Acceptor-1-sulfenyl-substituted 2-vinylcyclopropanes were isomerized to 6-sulfenyl-α,β-γ,δ-unsaturated carboxylic esters and nitriles via a C1-C2 bond fission and via a 1,5-sulfenyl shift using an acid catalyst.
Acid-promoted isomerisation of 1-acceptor-1-sulfenyl-substituted 2-vinylcyclopropanes with C1-C2 bond fission and novel 1,5-sulfenyl rearrangement
Iwama, Tetsuo,Matsumoto, Harutoshi,Kataoka, Tadashi
, p. 835 - 843 (2007/10/03)
1-Acceptor-1-sulfenyl-substituted vinylcyclopropanes 1 undergo C1-C2 bond fission and 1,5-sulfenyl rearrangement to give 6-sulfenyl-α,β;γ,δ-unsaturated carboxylic esters and nitriles 4 by treatment with acid. The reactions proceed smoothly by use of a sulfonic acid such as p-TsOH·H2O, CF3SO3H etc. in a non-polar solvent. The results, obtained from reactions of compounds 12 and 16, imply that the C1-C2 bond cleavage and deprotonation from the C2-methyl group of substrates 1 occur via a concerted process. The cross-over experiment showed that the 1,5-sulfenyl shift proceeds intermolecularly. Addition of a catalytic amount of m-MeC6H4SH improves the yield of the rearranged product 4c.
