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Reactions of nucleophiles with triarylpropenones and triarylbutenones
Author(s) -
Madhusudanan K. P.,
Jain Raka,
Mittal Shubhra,
Durani Susheel,
Kapil R. S.
Publication year - 1986
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210211203
Subject(s) - nucleophile , adduct , deprotonation , chemistry , carbon fibers , ionization , medicinal chemistry , ion , organic chemistry , polymer chemistry , photochemistry , catalysis , materials science , composite number , composite material
From a study of the reactions of nucleophiles with 1,2,3‐triaryl‐propenones and‐butenones in a chemical ionization source it has been found that stronger nucleophiles, such as, MeO − , EtO − and MeS − , attack the α,β‐unsaturated system at the β‐carbon (Michael addition) or the carbonyl carbon giving rise to tetrahedral adducts, while weaker nucleophiles, such as, Cl − form the adduct ion by H‐bonding with the β‐hydrogen. The effect of substituents and source temperature supports the operation of these processes. The triaryl butenone did not give the adduct ion with MeO − as deprotonation leads to a stable [M H] − ion.