Theoretical study of the regioselectivity in the diels-alder reactions of protoanemonin with substituted dienes

J. Ortí; V. Branchadell; R. M. Ortuño; A. Oliva; J. Font; J. Bertrán; J. J. Dannenberg

doi:10.1016/0166-1280(93)87176-E

Theoretical study of the regioselectivity in the diels-alder reactions of protoanemonin with substituted dienes

J. Ortí, V. Branchadell, R. M. Ortuño, A. Oliva, J. Font, J. Bertrán, J. J. Dannenberg

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

3 Citations (Scopus)

Abstract

The reactions leading to the Diels-Alder adducts of protoanemonin (5-methylene-2(5H)-furanone) with three unsymmetrical dienes isoprene, trans-piperylene ((E)-1,3-pentadiene), and (E)-2-methyl-1,3-pentadiene have been studied using the AM 1 molecular orbital method at both the RHF and open shell (3 × 3CI) levels. The results suggest that the reactions take place via very unsymmetrical transition states or similar biradicals. The regiospecificity of the dienes is well explained by the open shell calculations and is in reasonable agreement with the RHF calculations. © 1993.

Original language	English
Pages (from-to)	37-41
Journal	Journal of Molecular Structure: THEOCHEM
Volume	284
Issue number	1-2
DOIs	https://doi.org/10.1016/0166-1280(93)87176-E
Publication status	Published - 1 Jan 1993

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@article{f3d2c1622b1e4b9bb0bd1588a47dd415,

title = "Theoretical study of the regioselectivity in the diels-alder reactions of protoanemonin with substituted dienes",

abstract = "The reactions leading to the Diels-Alder adducts of protoanemonin (5-methylene-2(5H)-furanone) with three unsymmetrical dienes isoprene, trans-piperylene ((E)-1,3-pentadiene), and (E)-2-methyl-1,3-pentadiene have been studied using the AM 1 molecular orbital method at both the RHF and open shell (3 × 3CI) levels. The results suggest that the reactions take place via very unsymmetrical transition states or similar biradicals. The regiospecificity of the dienes is well explained by the open shell calculations and is in reasonable agreement with the RHF calculations. {\textcopyright} 1993.",

author = "J. Ort{\'i} and V. Branchadell and Ortu{\~n}o, {R. M.} and A. Oliva and J. Font and J. Bertr{\'a}n and Dannenberg, {J. J.}",

year = "1993",

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doi = "10.1016/0166-1280(93)87176-E",

language = "English",

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Theoretical study of the regioselectivity in the diels-alder reactions of protoanemonin with substituted dienes. / Ortí, J.; Branchadell, V.; Ortuño, R. M.; Oliva, A.; Font, J.; Bertrán, J.; Dannenberg, J. J.

In: Journal of Molecular Structure: THEOCHEM, Vol. 284, No. 1-2, 01.01.1993, p. 37-41.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Theoretical study of the regioselectivity in the diels-alder reactions of protoanemonin with substituted dienes

AU - Ortí, J.

AU - Branchadell, V.

AU - Ortuño, R. M.

AU - Oliva, A.

AU - Font, J.

AU - Bertrán, J.

AU - Dannenberg, J. J.

PY - 1993/1/1

Y1 - 1993/1/1

N2 - The reactions leading to the Diels-Alder adducts of protoanemonin (5-methylene-2(5H)-furanone) with three unsymmetrical dienes isoprene, trans-piperylene ((E)-1,3-pentadiene), and (E)-2-methyl-1,3-pentadiene have been studied using the AM 1 molecular orbital method at both the RHF and open shell (3 × 3CI) levels. The results suggest that the reactions take place via very unsymmetrical transition states or similar biradicals. The regiospecificity of the dienes is well explained by the open shell calculations and is in reasonable agreement with the RHF calculations. © 1993.

AB - The reactions leading to the Diels-Alder adducts of protoanemonin (5-methylene-2(5H)-furanone) with three unsymmetrical dienes isoprene, trans-piperylene ((E)-1,3-pentadiene), and (E)-2-methyl-1,3-pentadiene have been studied using the AM 1 molecular orbital method at both the RHF and open shell (3 × 3CI) levels. The results suggest that the reactions take place via very unsymmetrical transition states or similar biradicals. The regiospecificity of the dienes is well explained by the open shell calculations and is in reasonable agreement with the RHF calculations. © 1993.

U2 - 10.1016/0166-1280(93)87176-E

DO - 10.1016/0166-1280(93)87176-E

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VL - 284

SP - 37

EP - 41

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