Facile Preparation ofVicinalAllylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction
Publication type: Journal Article
Publication date: 1997-09-01
scimago Q2
wos Q2
SJR: 0.678
CiteScore: 7.0
Impact factor: 3.8
ISSN: 00092673, 13480634
General Chemistry
Abstract
Treatment of 2-(allyldimethylsiloxy)-1,1-dibromoalkane, which was easily prepared by an addition of aldehyde to an ethereal solution of (allyldimethylsilyl)dibromomethyllithium, with tributyltin hydride in the presence of catalytic amount of triethylborane afforded 1-oxa-2-silacycloheptane derivative selectively in good yield. On the other hand, cyclization of vinyldimethylsiloxy derivative resulted in a formation of 3-methyl-1-oxa-2-silacyclopentane. An addition of allyldiphenylsilanol to ethyl vinyl ether in the presence of N-iodosuccinimide provided 1-(allyldiphenylsiloxy)-1-ethoxy-2-iodoethane, which was also converted into a seven-membered ring product upon treatment with tributyltin hydride.
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Shinokubo H., OSHIMA K., Utimoto K. Facile Preparation ofVicinalAllylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction // Bulletin of the Chemical Society of Japan. 1997. Vol. 70. No. 9. pp. 2255-2263.
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Shinokubo H., OSHIMA K., Utimoto K. Facile Preparation ofVicinalAllylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction // Bulletin of the Chemical Society of Japan. 1997. Vol. 70. No. 9. pp. 2255-2263.
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RIS
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TY - JOUR
DO - 10.1246/bcsj.70.2255
UR - https://doi.org/10.1246/bcsj.70.2255
TI - Facile Preparation ofVicinalAllylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction
T2 - Bulletin of the Chemical Society of Japan
AU - Shinokubo, Hiroshi
AU - OSHIMA, Koichiro
AU - Utimoto, Kiitiro
PY - 1997
DA - 1997/09/01
PB - Oxford University Press
SP - 2255-2263
IS - 9
VL - 70
SN - 0009-2673
SN - 1348-0634
ER -
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BibTex (up to 50 authors)
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@article{1997_Shinokubo,
author = {Hiroshi Shinokubo and Koichiro OSHIMA and Kiitiro Utimoto},
title = {Facile Preparation ofVicinalAllylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction},
journal = {Bulletin of the Chemical Society of Japan},
year = {1997},
volume = {70},
publisher = {Oxford University Press},
month = {sep},
url = {https://doi.org/10.1246/bcsj.70.2255},
number = {9},
pages = {2255--2263},
doi = {10.1246/bcsj.70.2255}
}
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MLA
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Shinokubo, Hiroshi, et al. “Facile Preparation ofVicinalAllylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction.” Bulletin of the Chemical Society of Japan, vol. 70, no. 9, Sep. 1997, pp. 2255-2263. https://doi.org/10.1246/bcsj.70.2255.