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Synthesis and properties of an arylspiralene. A cisoid Z,Z-1,4-diphenyl-1,3-butadiene
β Scribed by Jin Liu; Robert S.H. Liu; Charles J. Simmons
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 312 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A synthetic route to the hindered Z,Z isomer of a cisoid 1,4-dipbenyl-1,3-butadiene iS described. Its crystal structure and properties are reported. 0 1997 Elsevier Science Ltd.
π SIMILAR VOLUMES
A stereospecific, highly efficient, generally applicable synthesis of z-ard El-alkoxy-1,3-butadienes involving dehydrative decarboxylations of 4,5\_unsaturated-2-alkoxy-3-hydroxy-carboxylic acids is described.
Ethyl propynoate reacted with esters of amino acids in methanolic solutions containing sodium acetate to yield the title compounds la-d in 40-52% yields. Some aromatic amines similarly reacted with ethyl propynoate to yield the dienes 3a-h in relatively poor yields (17-45%).
1Z,3Z)-Butyltelluro-4-methoxy-1,3-butadiene 2 was obtained by the hydrotelluration of (Z)-1-methoxybut-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z,3Z)-1butyltelluro-4-methoxy-1,3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a-d