Synthesis of Variously Substituted Spirobenzocyclobutenes

Phannarath Phansavath; Robert Stammler; Corinne Aubert; Max Malacria

doi:10.1055/s-1998-2048

Synthesis 1998; 1998(4): 436-443
DOI: 10.1055/s-1998-2048

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Synthesis of Variously Substituted Spirobenzocyclobutenes

Phannarath Phansavath^* , Robert Stammler, Corinne Aubert, Max Malacria

^*Université P. et M. Curie, Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Tour 44-54, B. 229, 4, place Jussieu 75252 Paris Cedex, France; Fax + 33(1 44)27 73 60; E-mail: malacria@ccr.jussieu.fr

Abstract

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The cobalt(I)-mediated cocyclization between bis(trimethylsilyl)ethyne and monocyclic diyne 8 led to new spirobenzocyclobutene 9. This quite stable compound was easily transformed into variously substituted spirobenzocyclobutenes which are versatile synthetic intermediates. The full details of the preparation of such compounds are presented.

cobalt(I) - [2+2+2] cycloaddition - spirobenzocyclobutenes - orthoquinodimethanes - [4+2] cyclisation

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