79306-18-6Relevant academic research and scientific papers
Magnesium amide-induced pummerer-type reactions of cyclopropyl sulfoxides. Synthesis of cyclopropanone dithioacetals
Kobayashi, Kazuhiro,Horita, Masatoshi,Irisawa, Susumu,Matsunaga, Akihiro,Morikawa, Osamu,Konishi, Hisatoshi
, p. 1367 - 1369 (2002)
The reaction of cyclopropyl phenyl sulfoxide with a magnesium amide, generated from ethylmagnesium bromide and diisopropylamine, gave 1-(phenylthio)cyclopropanol in 72% yield. When the diisopropylmagnesium reagent was treated with a thiol prior to an interaction with cyclopropyl phenyl sulfoxides, symmetrical and unsymmetrical cyclopropanone dithioacetals were produced in fair yields along with small quantities of the corresponding 1-(phenylthio)cyclopropanols.
The chemistry of small ring compounds. Part 43. Synthesis of 1-substituted cyclopropyl sulfides
Jorritsma, R.,Steinberg, H.,Boer, Th. J. de
, p. 184 - 194 (2007/10/02)
1-Hydroxy- and 1-halocyclopropyl sulfides can be conveniently prepared starting from cyclopropanone.Cyclopropyl sulfides with halogen or a dimethylsulfonium group in the α-position can be transformed into 1-substituted cyclopropyl sulfides with a variety of nucleophiles.This means that the usual difficulties encountered with nucleophilic substitution at three-membered rings - i.e. low rates and ring opening - are largely removed by the presence of an alkylthio group at the same ring carbon atom as the leaving group.
