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Reaction of 3‐nitro‐ and 3‐diethylphosphonocoumarin with phenacyl bromide. X‐ray molecular structure of 3‐nitro‐3,4‐phenacylidenecoumarin
Author(s) -
Rodios Nestor A.,
Bojilova Anka,
Terzis A.,
Raptopoulou C. P.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310505
Subject(s) - chemistry , nitro , phenacyl bromide , phenacyl , transfer agent , bromide , stereoselectivity , vinyl bromide , base (topology) , molecule , stereochemistry , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , alkyl , mathematics , monomer , polymer
3‐Nitro‐ and 3‐diethylphosphonocoumarins 4a,b react with phenacyl bromide stereoselectively under phase‐transfer conditions, in the presence of a base and of a transfer agent, to give the cyclopropyl derivatives 6 and 7 in good yields. A mechanistic explanation is given for the stereoselectivity of the reaction. The X‐ray molecular structure of compound 6a is also presented.