Premium
1‐(Dimethylamino)‐1,3‐butadiene, Darstellung und [4+2]‐Cycloaddition an trans ‐ß‐Nitrostyrol
Author(s) -
Potthoff Birgit,
Breitmaier Eberhard
Publication year - 1987
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19871200222
Subject(s) - chemistry , cycloaddition , wittig reaction , alkyl , medicinal chemistry , stereochemistry , stereoselectivity , proton , organic chemistry , catalysis , physics , quantum mechanics
The preparation of 1‐(dimethylamino)‐1,3‐butadienes 3 by Wittig alkenylation of 3‐(dimethylamino)acroleins 1 is described. The title compounds 3 undergo a [4+2] cycloaddition to trans ‐ß‐nitrostyrene ( 4 ) yielding regio‐ and stereoselectively 2‐alkyl‐3‐(dimethylamino)‐ trans ‐4‐nitro‐ trans ‐5‐phenylcyclohexenes 5 as apparent from proton‐proton coupling constants.