Synthesis of N,N-Dimethyl-2-(tributylstannyl)methyl-5-substituted Benzylamines as a Quinodimethane Precursor by the Reaction of N,N-Dimethyl-N-(tributylstannyl)methyl-4-substituted Benzylammonium Salts with Lithium Diisopropylamide.

Abstract

Reaction of N, N-dimethyl-N-(tributylstannyl)methyl-4-substituted benzylammonium salts 2 with lithium diisopropylamide (LDA) gave N, N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines 3 as the main products. Treatment of 3 with iodomethane followed by tetrabutylammonium fluoride (TBAF) in the presence of dimethyl fumarate gave the corresponding dimethyl trans-1, 2, 3, 4-tetrahydro-6-substituted naphthalene-2, 3-dicarboxylates 15 in good yields.