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Synthesis 2002(10): 1423-1433
DOI: 10.1055/s-2002-33109
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Klaus Banert*a, Stefan Grotha, Holger Hückstädtb, Jens Lehmanna, Jana Schlotta, Kai Vrobelb
a Institut für Chemie der Technischen Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany
Fax: +49(371)5311839; e-Mail: klaus.banert@chemie.tu-chemnitz.de;
b Fachbereich 8, Organische Chemie II, Universität Siegen, Adolf-Reichwein-Str., 57068 Siegen, Germany
Further Information

Publication History

Received 14 March 2002
Publication Date:
01 August 2002 (online)

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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]