Journal of Organic Chemistry p. 6065 - 6067 (1988)
Update date:2022-09-26
Topics:
Alonso, Ruben A.
Austin, E.
Rossi, Roberto A.
The photostimulated reaction of p-bromoanisole, p-iodoanisole, and 1-iodonaphthalene with the carbanion 2 of the cyclohexylideneacetonitrile 1 gave good yields of the isomeric substitution products 2-(p-anisyl)-1-cyclohexenylacetonitrile (3a), 2-(p-anisyl)cyclohexylideneacetonitrile (3b), 2-(1-naphthyl)-1-cyclohexenylacetonitrile (8a), and 2-(1-naphthyl)cyclohexylideneacetonitrile (8b).The substitution occured exclusively in the Cγ.These reactions do not occur in the dark, and the photostimulated reactions are inhibited by 1,4-dinitrobenzene.Thus it is proposed that these reactions occur by the SRN1 mechanism of nucleophilic substitution.
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