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A Facile One‐pot Synthesis of α ‐Halo, α ‐allylic Aldehydes from α , α ‐Dihalo Ketones Utilizing Allylic Zinc Bromide
Author(s) -
Wang Xiaolei,
Zhang Songlin
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201180466
Subject(s) - allylic rearrangement , chemistry , bromide , zinc bromide , zinc , medicinal chemistry , organic chemistry , catalysis
An efficient synthesis of various α ‐halo, α ‐allylic aldehydes from α , α ‐dihalo ketones using both cyclic (3‐bromocyclohex‐1‐ene zinc bromide and ( Z )‐3‐bromocyclobut‐1‐ene zinc bromide) and acyclic (allylzinc bromide and cinnamylzinc bromide) type of allylic organozinc bromide with DMF as base is described. A possible reaction mechanism is also proposed.