Toward 2-Thiophyne: Ketocarbene versus Hetaryne Intermediates from 2-(Trimethylsilyl)thiophen-3-yl Triflate.
Org Lett
; 23(19): 7376-7380, 2021 10 01.
Article
en En
| MEDLINE
| ID: mdl-34515492
ABSTRACT
The reaction of 2-(trimethylsilyl)thiophen-3-yl triflate with CsF in the presence of 2,3,4,5-tetraphenylcyclopentadienone affords 4,5,6,7-tetraphenylbenzo[b]thiophene, as it would be expected from the hypothesized generation and trapping of 2-thiophyne. However, a detailed experimental and computational study discards the intermediacy of this elusive 5-membered hetaryne. Instead, a complex mechanism involving the generation of an intermediate ketocarbene, which adds to the cyclopentadienone to give an isolable tricyclic intermediate, followed by thermal rearrangements, is proposed.
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Banco de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2021
Tipo del documento:
Article
País de afiliación:
España