Premium
Unusual reactions between chloroketenes and 1,3,5‐tri‐ tert ‐butylcyclopentadiene
Author(s) -
Dehmlow Eckehard Volker,
Bollmann Christof,
Neumann Beate,
Stammler HansGeorg
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199511270
Subject(s) - ketene , chemistry , triethylamine , acylation , medicinal chemistry , bicyclic molecule , chloride , organic chemistry , catalysis
Reaction of title compound 1 with dichloroketene resulted in a complex rearrangement to 2 when the ketene was generated from Cl 3 CCOCl/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 formal Diels‐Alder product 7 .