Rearrangement Reactions; 12: [1] Synthesis and Reactions of Isothiocyanate Substituted Allenes

Abstract

The first method for the preparation of isothiocyanate substituted allenes by [3,3] sigmatropic rearrangement of propargyl thiocyanates is described. These allenes undergo a variety of successive reactions such as ionic or sigmatropic isomerization, electrocyclic ring closure, cycloaddition, and electrophilic addition. Furthermore, intramolecular nucleophilic attack as well as treatment with external nucleophiles lead to heterocyclic products.

Key words

allenes - rearrangements - addition reactions - Diels-Alder reactions - heterocycles

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14

Compare with the rearrangement of 4-chloro-3-methylbuta-1,2-diene to 2-chloro-3-methylbuta-1,3-diene described in ref. [13]