A Computational Study on the Photochemical O-H Functionalization of Alcohols with Diazoacetates.
J Org Chem
; 87(10): 6832-6837, 2022 May 20.
Article
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| MEDLINE
| ID: mdl-35500213
ABSTRACT
In this computational study, we provide a detailed analysis of the underlying reaction mechanism and show that a singlet carbene is initially formed. Depending on the pKA of the alcohol, this singlet carbene can engage in direct protonation or enol formation to yield the O-H functionalization product. On the contrary, propargylic alcohols take up a dual role and form a complex with the carbene intermediate that leads to facile cyclopropenation reactions.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2022
Tipo del documento:
Article
País de afiliación:
Alemania