The intra-and intermolecular copper (I) catalyzed couplings of vinyl Grignards. A facile synthesis of pleiadiene and a synthesis of a conjugated 14-membered ring …

RH Mitchell, BN Ghose…

Index: Mitchell,R.H. et al. Canadian Journal of Chemistry, 1977 , vol. 55, p. 210 - 219

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Citation Number: 10

Abstract

Pleiadiene, 27, can be efficiently prepared in 45% yield by copper catalyzed intramolecular coupling of the bis-Grignard reagent of 1, 8-trans-(β-bromovinyl) naphthalene, 5. Also obtained in 6% yield is the unsaturated 14-membered ring compound 28. Whereas the bis (β-bromovinyl) compound 5 is readily available from 1, 8-divinylnaphthalene, α-bromovinyl compounds are obtained from divinylbenzenes. On coupling the Grignard reagent from 1, ...

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