Titanium-Catalyzed [4+2] and [6+2] Cycloadditions of 1,4-Bis(trimethylsilyl)buta-1,3-diyne
Jan-Willem F. Kaagman
1
,
Marco Rep
1
,
M. Horáček
2
,
PETR SEDMERA
3
,
J. Čejka
2
,
Vojtech Varga
2
,
Karel Mach
2
Publication type: Journal Article
Publication date: 2002-07-27
SJR: —
CiteScore: —
Impact factor: —
ISSN: 00100765, 12126950
General Chemistry
Abstract
The (C2H5)2AlCl/TiCl4 catalyst induces the [4+2] cycloaddition of butadiene or the [6+2] cycloaddition of 1,3,5-cycloheptatriene (CHT) to individual acetylenic moieties of 1,4-bis(trimethylsilyl)buta-1,3-diyne (BSD). Heating of the 2:1 butadiene adduct, bis(2-trimethylsilylcyclohexa-1,4-dien-1-yl), to 250 °C yields 2,2'-bis(trimethylsilyl)biphenyl. The 1:1 adduct of BSD with CHT, 7-trimethylsilyl-8-trimethylsilylethynylbicyclo[4.2.1]nona-2,4-diene, is obtained as virtually the only product if the initial molar ratio CHT : BD equal to 1.86 is used.
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Kaagman J. F. et al. Titanium-Catalyzed [4+2] and [6+2] Cycloadditions of 1,4-Bis(trimethylsilyl)buta-1,3-diyne // Collection of Czechoslovak Chemical Communications. 2002. Vol. 61. No. 12. pp. 1722-1728.
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Kaagman J. F., Rep M., Horáček M., SEDMERA P., Čejka J., Varga V., Mach K. Titanium-Catalyzed [4+2] and [6+2] Cycloadditions of 1,4-Bis(trimethylsilyl)buta-1,3-diyne // Collection of Czechoslovak Chemical Communications. 2002. Vol. 61. No. 12. pp. 1722-1728.
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TY - JOUR
DO - 10.1135/cccc19961722
UR - https://doi.org/10.1135/cccc19961722
TI - Titanium-Catalyzed [4+2] and [6+2] Cycloadditions of 1,4-Bis(trimethylsilyl)buta-1,3-diyne
T2 - Collection of Czechoslovak Chemical Communications
AU - Kaagman, Jan-Willem F.
AU - Rep, Marco
AU - Horáček, M.
AU - SEDMERA, PETR
AU - Čejka, J.
AU - Varga, Vojtech
AU - Mach, Karel
PY - 2002
DA - 2002/07/27
PB - Institute of Organic Chemistry & Biochemistry
SP - 1722-1728
IS - 12
VL - 61
SN - 0010-0765
SN - 1212-6950
ER -
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BibTex (up to 50 authors)
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@article{2002_Kaagman,
author = {Jan-Willem F. Kaagman and Marco Rep and M. Horáček and PETR SEDMERA and J. Čejka and Vojtech Varga and Karel Mach},
title = {Titanium-Catalyzed [4+2] and [6+2] Cycloadditions of 1,4-Bis(trimethylsilyl)buta-1,3-diyne},
journal = {Collection of Czechoslovak Chemical Communications},
year = {2002},
volume = {61},
publisher = {Institute of Organic Chemistry & Biochemistry},
month = {jul},
url = {https://doi.org/10.1135/cccc19961722},
number = {12},
pages = {1722--1728},
doi = {10.1135/cccc19961722}
}
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MLA
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Kaagman, Jan-Willem F., et al. “Titanium-Catalyzed [4+2] and [6+2] Cycloadditions of 1,4-Bis(trimethylsilyl)buta-1,3-diyne.” Collection of Czechoslovak Chemical Communications, vol. 61, no. 12, Jul. 2002, pp. 1722-1728. https://doi.org/10.1135/cccc19961722.