2,3-Pyridyne Formation by Fluoride-Induced Desilylation-Elimination

Abstract

The formation of 2,3-pyridyne by a desilylation-elimination sequence employing anhydrous CsF is reported.

Notes

Purchased from Aldrich.

All yields are unoptimized. The cycloaddition reactions gave no other identifiable products other than the anticipated cycloadducts. Apparently, 2,3-pyridyne is much more prone to polymerization than benzyne since reactions involving the latter intermediate usually proceeding in much higher yield. The analytical data for compounds 6, 7, 8, 9, and 11 was identical to that which has been reported previously in the literature.