volume 121 issue 3 pages 285-291

Reaction of trimethylsilyl azide with bridged bicyclic olefins

William F. Peterson 1
Barry Arkles 1
Stephen S Washburne 2
Publication typeJournal Article
Publication date1976-11-01
scimago Q3
wos Q2
SJR0.385
CiteScore4.1
Impact factor2.4
ISSN0022328X, 18728561
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Bridged bicyclic olefins were found to undergo facile 1,3-cycloaddition reaction with trimethylsilyl azide. Norbornene produced cis,exo -1-trimethylsilyl-4,7-methano-3a,4,5,6,7,7a-hexahydrobenzotriazole, while norbornadiene formed a diadduct with cis,exo -stereochemistry, together with 2-trimethylsilyl-1,2,3-triazole produced by a retro-Diels—Alder reaction of an intermediate mono-adduct. Dicyclopentadiene reacted only at the norbornene position while α-pinene did not react with trimethylsilyl azide. In contrast to aryl- and sulfonyl-azide adducts of norbornene derivatives, which decompose upon heating the present adducts were recovered unchanged after prolonged treatment at 205°C.
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GOST Copy
Peterson W. F., Arkles B., Washburne S. S. Reaction of trimethylsilyl azide with bridged bicyclic olefins // Journal of Organometallic Chemistry. 1976. Vol. 121. No. 3. pp. 285-291.
GOST all authors (up to 50) Copy
Peterson W. F., Arkles B., Washburne S. S. Reaction of trimethylsilyl azide with bridged bicyclic olefins // Journal of Organometallic Chemistry. 1976. Vol. 121. No. 3. pp. 285-291.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/s0022-328x(00)85082-2
UR - https://doi.org/10.1016/s0022-328x(00)85082-2
TI - Reaction of trimethylsilyl azide with bridged bicyclic olefins
T2 - Journal of Organometallic Chemistry
AU - Peterson, William F.
AU - Arkles, Barry
AU - Washburne, Stephen S
PY - 1976
DA - 1976/11/01
PB - Elsevier
SP - 285-291
IS - 3
VL - 121
SN - 0022-328X
SN - 1872-8561
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{1976_Peterson,
author = {William F. Peterson and Barry Arkles and Stephen S Washburne},
title = {Reaction of trimethylsilyl azide with bridged bicyclic olefins},
journal = {Journal of Organometallic Chemistry},
year = {1976},
volume = {121},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/s0022-328x(00)85082-2},
number = {3},
pages = {285--291},
doi = {10.1016/s0022-328x(00)85082-2}
}
MLA
Cite this
MLA Copy
Peterson, William F., et al. “Reaction of trimethylsilyl azide with bridged bicyclic olefins.” Journal of Organometallic Chemistry, vol. 121, no. 3, Nov. 1976, pp. 285-291. https://doi.org/10.1016/s0022-328x(00)85082-2.