New and efficient catalytic route to bicyclo[3.3.0]octa-1,5-dien-3-ones

Iwao Ojima; Dora Fracchiolla Kass; Jiawang Zhu

doi:10.1021/om960471n

New and efficient catalytic route to bicyclo[3.3.0]octa-1,5-dien-3-ones

Iwao Ojima
, Dora Fracchiolla Kass
, Jiawang Zhu

Chemistry

Stony Brook University

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	5191-5195
Number of pages	5
Journal	Organometallics
Volume	15
Issue number	24
DOIs	https://doi.org/10.1021/om960471n
State	Published - Nov 26 1996

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title = "New and efficient catalytic route to bicyclo[3.3.0]octa-1,5-dien-3-ones",

abstract = "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.",

author = "Iwao Ojima and Kass, \{Dora Fracchiolla\} and Jiawang Zhu",

year = "1996",

month = nov,

day = "26",

doi = "10.1021/om960471n",

language = "English",

volume = "15",

pages = "5191--5195",

journal = "Organometallics",

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TY - JOUR

T1 - New and efficient catalytic route to bicyclo[3.3.0]octa-1,5-dien-3-ones

AU - Ojima, Iwao

AU - Kass, Dora Fracchiolla

AU - Zhu, Jiawang

PY - 1996/11/26

Y1 - 1996/11/26

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0000828708

U2 - 10.1021/om960471n

DO - 10.1021/om960471n

M3 - Article

AN - SCOPUS:0000828708

SN - 0276-7333

VL - 15

SP - 5191

EP - 5195

JO - Organometallics

JF - Organometallics

IS - 24

ER -

New and efficient catalytic route to bicyclo[3.3.0]octa-1,5-dien-3-ones

Abstract

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