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  Ethoxyacetylene and ethyl vinyl ether, dipolarophiles of opposite regiochemistry in diazomethane cycloadditions

Sustmann, R., Sicking, W., & Felderhoff, M. (1990). Ethoxyacetylene and ethyl vinyl ether, dipolarophiles of opposite regiochemistry in diazomethane cycloadditions. Tetrahedron, 46(3), 783-792. doi:10.1016/S0040-4020(01)81361-2.

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 Creators:
Sustmann, Reiner1, Author
Sicking, Willi1, Author
Felderhoff, Michael1, 2, Author              
Affiliations:
1Institut für Organische Chemie der Universität Essen, Postfach 103 764, D-43 Essen West Germany, ou_persistent22              
2Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445589              

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 Abstract: Diazomethane adds to ethoxyacetylene to give a 96 : 4 mixture in favor of 4-ethoxypyrazole (3) which had been identified as the only product in a previous study. This result contrasts the behavior of ethyl vinyl ether which gives 3-ethoxy-1-pyrazoline (2). Transition structures for the four possible regioisomers are determined by MNDO-PM3 calculations. The regioselectivity is explained on the basis of the PM3 calculations and their perturbational analysis using the program PERVAL. Distortions of the dipolarophiles in the transition structures due to closed-shell repulsions lead to FMO interactions which favor the experimental regiochemistry.

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Language(s): eng - English
 Dates: 2001-03-151990
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/S0040-4020(01)81361-2
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Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 46 (3) Sequence Number: - Start / End Page: 783 - 792 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773