Synthesis of 5‐Methoxy‐ and 5‐(Dialkylamino)bicyclo[3.2.0]hept‐2‐en‐6‐one Derivatives by cine Substitution with Methoxide Anions and Dialkylamines

verfasst von

Holger Butenschön

Abstract

exo‐7‐Chloro‐endo‐7‐phenylbicyclo[3.2.0]hept‐2‐en‐6‐one (5) undergoes cine substitution reactions with methoxide anions and with dialkylamines to give 5‐methoxy or 5‐dialkylamino derivatives 13, 14, 16–19 in high yield. While attempts directed to an acetalization have failed, the addition of Grignard reagents to the methoxy derivatives proceeds stereoselectively in high yield. Hydrochlorides 20/21 lose amine at 110°C to form 2‐phenyltropone 22. Thermolysis of diethylamino derivative 24 at 170°C (temperature determined by DSC) results in the formation of the dienaminone 25.

Externe Organisation(en)

Max-Planck-Institut für Kohlenforschung

Typ

Artikel

Journal

Chemische Berichte

Band

127

Seiten

137-144

Anzahl der Seiten

8

ISSN

0009-2940

Publikationsdatum

01.1994

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Allgemeine Chemie

Elektronische Version(en)

https://doi.org/10.1002/cber.19941270122 (Zugang: Unbekannt)