Re-examination of the Cycloaddition of Cycloheptatriene with Maleic Anhydride
Тип публикации: Journal Article
Дата публикации: 1971-11-01
scimago Q2
wos Q2
БС1
SJR: 0.678
CiteScore: 7.0
Impact factor: 3.8
ISSN: 00092673, 13480634
General Chemistry
Краткое описание
Cycloaddition of cycloheptatriene to maleic anhydride was re-examined and found to produce, in addition to the reported main product anti-tricyclo[3.2.2.02,4]non-6-endo-8,endo-9-dicarboxylic anhydride (1), the exo, exo isomer of this compound (4) and bicyclo[3.2.2]nona-2,6-diene-endo-8,endo-9-dicarboxylic anhydride (5). Evidence for these structures involving the orientation of the cyclopropane ring in 1 and 4 and the configuration of the carboxylic anhydride was provided by PMR spectroscopy using the intramolecular nuclear Overhauser effect and paramagnetic induced shift due to tris(dipivalomethanato)europium(III). The structure assignment by Alder and Jacobs for 1 was found to be correct, but not the one by Schenk et al The difference in free energies of activation leading to 1 and 4 was determined.
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Ishitobi H. et al. Re-examination of the Cycloaddition of Cycloheptatriene with Maleic Anhydride // Bulletin of the Chemical Society of Japan. 1971. Vol. 44. No. 11. pp. 2993-3000.
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Ishitobi H., Tanida H., Tori K., TSUJI T. Re-examination of the Cycloaddition of Cycloheptatriene with Maleic Anhydride // Bulletin of the Chemical Society of Japan. 1971. Vol. 44. No. 11. pp. 2993-3000.
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TY - JOUR
DO - 10.1246/bcsj.44.2993
UR - https://doi.org/10.1246/bcsj.44.2993
TI - Re-examination of the Cycloaddition of Cycloheptatriene with Maleic Anhydride
T2 - Bulletin of the Chemical Society of Japan
AU - Ishitobi, Hiroyuki
AU - Tanida, Hiroshi
AU - Tori, Kazuo
AU - TSUJI, Teruji
PY - 1971
DA - 1971/11/01
PB - Oxford University Press
SP - 2993-3000
IS - 11
VL - 44
SN - 0009-2673
SN - 1348-0634
ER -
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@article{1971_Ishitobi,
author = {Hiroyuki Ishitobi and Hiroshi Tanida and Kazuo Tori and Teruji TSUJI},
title = {Re-examination of the Cycloaddition of Cycloheptatriene with Maleic Anhydride},
journal = {Bulletin of the Chemical Society of Japan},
year = {1971},
volume = {44},
publisher = {Oxford University Press},
month = {nov},
url = {https://doi.org/10.1246/bcsj.44.2993},
number = {11},
pages = {2993--3000},
doi = {10.1246/bcsj.44.2993}
}
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Ishitobi, Hiroyuki, et al. “Re-examination of the Cycloaddition of Cycloheptatriene with Maleic Anhydride.” Bulletin of the Chemical Society of Japan, vol. 44, no. 11, Nov. 1971, pp. 2993-3000. https://doi.org/10.1246/bcsj.44.2993.