Stereoselective polycyclisations of allyl and enyne silanes: evidence for a bicyclo[3.2.0]hept-1(7)ene structure
The intramolecular copper(I)-catalyzed [2+2]-photocycloaddition of diphenyldiallylsilane ( 1) (or tetraallylsilane ( 4)) led to sila-3-bicyclo[3.2.0]heptane ( 3) (or to spiro analogous 6) in the cis (or cis– cis) configuration whereas the α,ω-diiodide ( 2) obtained by cyclozirconation of 1 (or from...
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Published in | Journal of organometallic chemistry Vol. 643; pp. 324 - 330 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
LAUSANNE
Elsevier B.V
01.02.2002
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | The intramolecular copper(I)-catalyzed [2+2]-photocycloaddition of diphenyldiallylsilane (
1) (or tetraallylsilane (
4)) led to sila-3-bicyclo[3.2.0]heptane (
3) (or to spiro analogous
6) in the
cis (or
cis–
cis) configuration whereas the α,ω-diiodide (
2) obtained by cyclozirconation of
1 (or from the homologous tetraiodide
5) followed by addition of
n-BuLi, produced the sila-3-bicyclo[3.2.0]heptane (
3) (or to the spiro analogous
6) in the
trans (or
trans–
trans configuration). The same cyclozirconation reaction, starting from the hetero enyne
7, selectively led to the highly strained silacyclobutene moiety
15 which represents the first stable hetero bicyclo[3.2.0]hept-1(7)ene skeleton, hypothetical intermediate in metathesis reactions.
The spirosilanes in
cis–
cis or
trans–
trans configuration are obtained by two appropriate methods. The cyclozirconation of enyne silane, led to silacyclobutene which represents the first stable hetero bicyclo[3.2.0]hept-1(7)ene skeleton, hypothetical intermediate in metathesis reaction. |
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ISSN: | 0022-328X 1872-8561 |
DOI: | 10.1016/S0022-328X(01)01393-6 |