The Journal of Organic Chemistry

2-Thiazolines in organic synthesis. Synthesis of mono-, di-, and trialkylacetaldehydes

AI Meyers, JL Durandetta

Index: Meyers,A.I.; Durandetta,J.L. Journal of Organic Chemistry, 1975 , vol. 40, p. 2021 - 2025

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Citation Number: 44

Abstract

Metalation of 2-methyl-2-thiazoline (1) using n-butyllithium at low temperature furnishes a nucleophilic thiazoline anion which may be alkylated to n-(alkylmethy1) thiazolines (2). This process may be repeated to produce dialkylated (5 and 9) and trialkylated thiazolines 14. Reduction of the C= N link was readily accomplished using aluminum amalgam in wet ether affording the thiazolidines 3, 6, and 15, respectively. Release of the aldehydes 4, 7, 10, ...

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