Synthesis of a Bicyclo[8.3.1]enediyne via Chromium-Mediated Dearomatization of 2,6-Bis(trimethylsilyl)anisole

Lavy, Severine; Pérez-Luna, Alejandro; Kundig, Ernst Peter

doi:10.1055/s-0028-1083513

Scientific article

Letter

English

Synthesis of a Bicyclo[8.3.1]enediyne via Chromium-Mediated Dearomatization of 2,6-Bis(trimethylsilyl)anisole

ContributorsLavy, Severine; Pérez-Luna, Alejandro; Kundig, Ernst Peter

Published inSynlett, no. 17, p. 2621-2624

Publication date2008

Abstract

A novel bicyclo[8.3.1]enediyne was readily synthesized by chromium-mediated dearomatization of 2,6-bis(trimethylsilyl)anisole. The enediyne undergoes Bergman cyclization with a half-life of 14.4 hours at 142 °C.

Keywords

Enediynes
Dearomatization
[Cr(arene)(CO)3] complexes
Bergman cyclization
Nicholas reaction

Affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

LAVY, Severine, PÉREZ-LUNA, Alejandro, KUNDIG, Ernst Peter. Synthesis of a Bicyclo[8.3.1]enediyne via Chromium-Mediated Dearomatization of 2,6-Bis(trimethylsilyl)anisole. In: Synlett, 2008, n° 17, p. 2621–2624. doi: 10.1055/s-0028-1083513

Article

Identifiers

PID : unige:7961
DOI : 10.1055/s-0028-1083513

ISSN of the journal0936-5214

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Synthesis of a Bicyclo[8.3.1]enediyne via Chromium-Mediated Dearomatization of 2,6-Bis(trimethylsilyl)anisole

A novel bicyclo[8.3.1]enediyne was readily synthesized by chromium-mediated dearomatization of 2,6-bis(trimethyl­silyl)anisole. The enediyne undergoes Bergman cyclization with a half-life of 14.4 hours at 142 °C.

Technical informations

A novel bicyclo[8.3.1]enediyne was readily synthesized by chromium-mediated dearomatization of 2,6-bis(trimethylsilyl)anisole. The enediyne undergoes Bergman cyclization with a half-life of 14.4 hours at 142 °C.