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Die Addition von Nucleophilen an Alkinderivate mit Push‐pull‐Gruppen
Author(s) -
Niederhauser Andreas,
Frey Alfred,
Neuenschwander Markus
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560310
Subject(s) - chemistry , alkyne , nucleophile , adduct , nucleophilic addition , addition reaction , medicinal chemistry , michael reaction , primary (astronomy) , stereochemistry , organic chemistry , catalysis , physics , astronomy
The preparative aspects of the addition of nucleophiles to alkyne‐derivatives having both push‐ and pull‐groups ( 1 ) are discussed: The addition of primary and secondary amines as well of aliphatic alcohols to the alkyne‐derivatives 1 in most cases predominantly yields the Michael ‐adducts 2 – 10 . The importance of a side‐reaction consisting in an addition of amines to C(2) of the alkyne‐derivatives 1 increases in the series 1c ≪ 1b < 1a and is controlled by stereoelectronic effects. The spectroscopic properties of the compounds 2 – 10 are given.