ISSN:
1434-193X
Keywords:
Autoxidation
;
Dimerisation
;
Enolates
;
Isomerisations
;
Strained molecules
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
3-(Phenylsulfanyl)benzvalene (6) was prepared by de-hydrochlorination from the adduct 5 of phenylsulfenyl chloride to benzvalene (4) with potassium tert-butoxide. An autoxidation transformed 6 readily to the tricyclo[3.1.0.02,6]hexanone 7, which was converted into its 4-deuterio derivative [4-D]-7 under mild conditions. The treatment of 7 with potassium hydride in the presence of methyl iodide and 1,3-diiodopropane afforded the alkyl derivatives 9 and 10, respectively, of 7. In the absence of an active alkylating agent, the reaction of 7 with potassium hydride gave rise to the bicyclohexyltricyclohexanes 11 being dimers of 7. Presumably, this process is initiated by the rearrangement of 7 to the bicyclohexenone 13 and completed by a Michael addition of 7 to 13.
Type of Medium:
Electronic Resource
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