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Reaction of α,β‐unsaturated ketones with cerium(IV) salts in alcohol
Author(s) -
Horiuchi C. Akira,
Saitoh Yoshikazu,
Utsukihara Takamitsu,
Takahashi Shigeo,
Matsushita Masatoshi,
He Liangyou,
Takahashi T. Tomoyoshi,
Hashimoto Chikao,
Sugiyama Takashi,
Nozaki Sukekatsu
Publication year - 2006
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1096
Subject(s) - chemistry , cerium , alcohol , acetal , medicinal chemistry , alkoxy group , organic chemistry , alkyl
Reaction of α,β‐unsaturated ketones with cerium(IV) salts or lanthanide triflates in alcohols gave good yields of the corresponding β‐alkoxy compounds. In the case of 2‐cyclopentenone and 2‐cyclohexenone, the 1,1,3‐trialkoxy acetal derivatives were obtained preferentially accompanied by β‐alkoxyketone, except 2‐cycloheptenone. However, in the reaction of 2‐cycloheptenone with alcohol using cerium(IV) sulfate (CS)‐molecular sieve, 1,1,3‐trialkoxy derivatives were obtained. Also, in the cases of 1‐penten‐3‐one, 4‐hexen‐3‐one and 3‐hepten‐2‐one, 1,1,3‐trialkoxy derivatives were obtained preferentially. Copyright © 2006 John Wiley & Sons, Ltd.