New and Efficient Catalytic Route to Bicyclo[3.3.0]octa-1,5-dien-3-ones

The silylcarbobicyclization of 4,4-disubstituted 1,6-heptadiynes with tert-butyldimethylsilane catalyzed by Rh(acac)(CO)2, Co2Rh2(CO)12, or (t-BuNC)4RhCo(CO)4 under 50 atm of carbon monoxide gives the corresponding novel 7,7-disubstituted 2-silylbicyclo[3.3.0]octa-1,5-dien-3-ones in good yields. A p...

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Bibliographic Details
Published in:Organometallics 1996-11, Vol.15 (24), p.5191-5195
Main Authors: Ojima, Iwao, Kass, Dora Fracchiolla, Zhu, Jiawang
Format: Article
Language:English
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Summary:The silylcarbobicyclization of 4,4-disubstituted 1,6-heptadiynes with tert-butyldimethylsilane catalyzed by Rh(acac)(CO)2, Co2Rh2(CO)12, or (t-BuNC)4RhCo(CO)4 under 50 atm of carbon monoxide gives the corresponding novel 7,7-disubstituted 2-silylbicyclo[3.3.0]octa-1,5-dien-3-ones in good yields. A possible mechanism is proposed. The unique feature of this strained skeleton is discussed on the basis of 13C NMR and X-ray crystallographic analyses.
ISSN:0276-7333
1520-6041
DOI:10.1021/om960471n