1‐(Dimethylamino)‐1,3‐butadiene, Darstellung und [4+2]‐Cycloaddition an  trans ‐ß‐Nitrostyrol | Zendy

Potthoff Birgit | Zendy; Breitmaier Eberhard | Zendy

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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.

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