Chemoselectivity in the synthesis of thiocyanates and isothiocyanates: the reaction of alkenes with benzeneselenenyl thiocyanate in methylene chloride
Open Access
- 15 August 1979
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 57 (16) , 2145-2153
- https://doi.org/10.1139/v79-344
Abstract
The reactions of benzeneselenenyl thiocyanate with some simple alkylsubstituted acyclic and cyclic alkenes have been investigated, and the relative distribution of isomeric adducts determined. The relative distribution of β-thiocyanatoalkyl phenyl selenide to β-isothiocyanatoalkyl phenyl selenide is found to be dependent upon the degree of substitution of the initial alkene. Thus mono- and disubstituted alkenes favour formation of the thiocyanato species, whereas tri- and tetrasubstituted alkenes yield isothiocyanato adducts almost exclusively. Stereospecific anti addition was established in all cases except that of tricyclo[4.2.2.02,5]deca-3,9-diene-7,8-dicarboxylic anhydride which gives a 33:67 mixture of cis and trans adducts.Keywords
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