UNUSUAL REACTIONS BETWEEN CHLOROKETENES AND 1,3,5-TRI-TERT-BUTYLCYCLOPENTADIENE

Authors
DEHMLOW EV BOLLMANN C NEUMANN B STAMMLER HG
Citation
Ev. Dehmlow et al., UNUSUAL REACTIONS BETWEEN CHLOROKETENES AND 1,3,5-TRI-TERT-BUTYLCYCLOPENTADIENE, Liebigs Annalen, (11), 1995, pp. 1915-1919
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
11
Year of publication
1995
Pages
1915 - 1919
Database
ISI
SICI code
0947-3440(1995):11<1915:URBCA1>2.0.ZU;2-Z
Abstract
Reaction of title compound 1 with dichloroketene resulted in a complex rearrangement to 2 when the ketene was generated from Cl3CCOCl/Zn. In contrast, treatment of 1 with the ketene produced from dichloroacetyl chloride/triethylamine gave a bicyclo[3.2.0]heptenone (3) along with acylation product 4. Reaction of monochloroketene with 1 afforded the ''normal'' endo-chloro compound 6 which thermally rearranged to the fo rmal Diels-Alder product 7.