70048-58-7Relevant academic research and scientific papers
THE 1,1-BIS(ALKYLTHIO)ALKENYL GROUP AS INITIATOR IN THE ELECTROPHILIC CYCLIZATION OF POLYENES
Mizyuk, V. L.
, p. 1098 - 1107 (2007/10/02)
The Z- and E-6-methyl-9-(1,3-dithia-2-cyclohexylidene)-5-nonen-2-ones were obtained from Z- and E-4-methyl-8-oxo-4-nonen-1-als and (1,3-dithia-2-cyclohexylidene)trialkoxyphosphoranes in the Wittig reaction.Their electrophylic cyclization by the action of trifluoroacetic acid with various methods for stabilization of the bicyclic oxonium salts was studied.Hydrolysis leads to 3-methyl-2-(3-oxobutyl)-2-cyclohexen-1-one, while reduction with triethylsilane or sodium borohydride gives 1,3-dimethyl-7-(1,5-dithia-1,5-pentamethylene)-2-oxabicyclodecanes as the main reaction products.A stereochemical reaction path is proposed.It was concluded that the 1-bis(alkylthio)alkenyl group is an effective initiator of the electrophilic cyclization of 1,5-polyenes.
