Competing nature of intramolecular [4 + 2] and [3 + 2] cycloaddition reactions: a theoretical study Научная публикация
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Journal of Physical Organic Chemistry
ISSN: 0894-3230 , E-ISSN: 1099-1395 |
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| Вых. Данные | Год: 2003, Том: 16, Номер: 4, Страницы: 253-263 Страниц : 11 DOI: 10.1002/poc.613 | ||
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Реферат:
Comparative study of the intramolecular alkyne triple bond addition reaction to the conjugated C≡C—CHX moiety (X = CH2,O,S,NH) revealed that two different pathways are possible in the system, namely [4 + 2] and [3 + 2] cycloaddition reactions. The energetically preferred pathway for enynes (X = CH2) involves [4 + 2] cycloaddition leading to benzene derivatives, whereas heteroatom-substituted substrates undergo [3 + 2] cycloaddition resulting in an five-membered aromatic ring in the final product. This paper reports a detailed mechanistic study based on full potential energy surface calculations at the MP2 and B3LYP theory levels, with MP4(SDTQ) energy evaluation. The effect of solvent was included within the PCM approach. Copyright © 2003 John Wiley & Sons, Ltd.
Библиографическая ссылка:
Ananikov V.P.
Competing nature of intramolecular [4 + 2] and [3 + 2] cycloaddition reactions: a theoretical study
Journal of Physical Organic Chemistry. 2003. V.16. N4. P.253-263. DOI: 10.1002/poc.613 Scopus OpenAlex
Competing nature of intramolecular [4 + 2] and [3 + 2] cycloaddition reactions: a theoretical study
Journal of Physical Organic Chemistry. 2003. V.16. N4. P.253-263. DOI: 10.1002/poc.613 Scopus OpenAlex
Идентификаторы БД:
| Scopus: | 2-s2.0-0037389537 |
| OpenAlex: | W2167124429 |