1,1-bis(alkylthio)alkenyl group is an initiator in the electrophilic cyclization of polyenes

Journal Article · Thu Nov 10 04:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5887748

Mizyuk, V L

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 electrophilic cyclization by the action of trifluoroacetic acid with various methods for stabilization of the bicyclic oxonium salts were 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-oxa(4.4.0)bicyclodecanes 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.

• OSTI ID: 5887748
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:6; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETIC ACID
ACTIVATION ENERGY
ALDEHYDES
BINDING ENERGY
CARBOXYLIC ACIDS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL BONDS
CHEMICAL REACTIONS
DEHYDROCYCLIZATION
DOUBLE BONDS
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
FERMIONS
HYDROCARBONS
INFRARED SPECTRA
KETONES
LEPTONS
MONOCARBOXYLIC ACIDS
NMR SPECTRA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POLYENES
SPECTRA
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
ULTRAVIOLET SPECTRA
VALENCE