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The preparation of 1,2-diphenylcyclobutene and 1,2-diphenylcyclohexene by the reductive coupling of the corresponding diketones with TiCl3-LiAlH4

✍ Scribed by A.L. Baumstark; E.J.H. Bechara; M.J. Semigran

Publisher
Elsevier Science
Year
1976
Tongue
French
Weight
82 KB
Volume
17
Category
Article
ISSN
0040-4039

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✦ Synopsis

The intermolecular reductive coupling of carbonyls to olefins has been accomeliehed by a "umber of reagents1 of which the mst general is TiCL,-UAW+, Id,2 . MC Hurry swsted2, in 1974, the use of this reagent to couple 1,s and 1,6-diketones to form cyclic alefins. Recently, MC Murry and Fleming have shown3 that acrive Ti' powder (TIC13-K') ca" achieve the intramolecular reductive coupling of a 1,5-dicarbonyl to form a cyclopenrene derivative. They also prepared3 cycloheptene and a cyclohexene derivative by reduction of the corresponding 1,2-dials with the same reagenr. We became intaested in olefi" synthesis I" connection with "UT work on diaxetanes4 and wish to report the one-step preparation of 1,2-diphenylcyclobutene (reaction 1) and 1,2diphenylcyclohexene (reaction 2) by the reaction of TIC13-~IA1H4 with the corresponding diketones in moderate yields.

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