79306-19-7Relevant academic research and scientific papers
The chemistry of small ring compounds. Part 46. Reduction of 1-halocyclopropyl sulfides by thiolates
Jorritsma, R.,Steinberg, H.,Boer, Th. J. de
, p. 288 - 298 (2007/10/02)
The reaction of 1-halocyclopropyl sulfides with sodium alkanethiolates in protic or aprotic solvents leads to high yields of cyclopropyl sulfides, in which halogen has been replaced by hydrogen.The complementary oxidized product is, in most cases, the thioketone or thioaldehyde derived from the alkanethiolate.The reduction is unaffected by radical scavengers or by one-electron donors.Reaction kinetics indicate that the reduction proceeds via the 1-(alkylthio)cyclopropyl cation.A mechanism is discussed (Scheme 9) in which this ambident cation is attacked by thiolate on sulfur.In the intermediary sulfonium ylid an intramolecular hydrogen shift leads to the observed products.
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.
