Cycloaddition of Dialkylalumanyl Anion toward Unsaturated Hydrocarbons in (1+2) and (1+4) Modes.
Chemistry
; 26(10): 2174-2177, 2020 Feb 17.
Article
em En
| MEDLINE
| ID: mdl-31880356
ABSTRACT
The reactivity of dialkylalumanyl anion (1) towards naphthalene, anthracene, diphenylacetylene, and (E)/(Z)-stilbenes was investigated. The compoundâ
1 reacts with naphthalene and anthracene through (1+4) cyclization, giving Al-containing norbornadiene derivatives. In the reaction of 1 with diphenylacetylene and (E)/(Z)-stilbenes, (1+2) cyclization proceeded to form Al-C-C three-membered rings. Cyclization toward (E)- or (Z)-stilbenes solely gave a trans-cycloadduct. DFT calculations revealed that the cycloaddition of 1 with (Z)-stilbene proceeds via a single transition state with a carbanion character, which results in the selectivity towards the trans-cycloadduct.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2020
Tipo de documento:
Article
País de afiliação:
Japão