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Unusual cerium(III) chloride‐promoted reactions of alkenyl grignard reagents or alkenyl‐lithiums with 1,3‐diphenyl‐2‐propanone: Formation and trapping of diorganometallic species
Author(s) -
Imamoto Tsuneo,
Hatajima Toshihiko,
Ogata Koreharu,
Nishiura Masayoshi
Publication year - 1995
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.590090512
Subject(s) - chemistry , cerium , medicinal chemistry , magnesium bromide , ketone , bromide , tetrahydrofuran , phenylmagnesium bromide , yield (engineering) , diphenyl diselenide , lithium (medication) , organic chemistry , reagent , magnesium , materials science , solvent , metallurgy , medicine , selenium , endocrinology
Treatment of vinylmagnesium chloride with anhydrous cerium(III) chloride in tetrahydrofuran at −20°C, followed by reaction with 1,3‐diphenyl‐2‐propanone, afforded ( Z )‐2,7‐dibenzyl 1,8‐diphenyl‐4‐octene‐2,7‐diol and ( Z )‐2,7‐dibenzyl‐1,8‐diphenyl‐4,6‐octadien‐2‐ol in 19% and 9% yield, respectively. Isopropenyl‐magnesium bromide underwent trimerization on treatment with cerium chloride at 20°C, and the subsequent reaction with the same ketone provided ( Z , Z )‐2,9‐dibenzyl‐4,5,7‐trimethyl‐1,10‐diphenyl‐4,6‐decadiene‐2, 9‐diol in 22% yield. Under similar conditions, the reaction of 2‐methyl‐1‐propenylmagnesium bromide provided ( Z )‐2,6‐dibenzyl‐4‐methyl‐1,7‐diphenyl‐3,5‐heptadien‐2‐ol in 7% yield. Vinyl‐lithium and isopropenyl‐lithium were also subjected to dimerization by the action of cerium chloride, and the generated diorganometallic species were trapped by 1,3‐diphenyl‐2‐propanone.