448922-64-3Relevant academic research and scientific papers
Synthesis of 2-indanones via [4 + 1] annulation reactions of (trialkylsilyl)arylketenes
Dalton, Audra M.,Zhang, Yongjun,Davie, Christopher P.,Danheiser, Rick L.
, p. 2465 - 2468 (2007/10/03)
(Matrix presented) (Trialkylsilyl)arylketenes combine with (trimethylsilyl)diazomethane in a new [4 + 1] annulation process leading to 2-indanone derivatives. The (trialkylsilyl)arylketene annulation substrates are available via the photochemical Wolff rearrangement of α-silyl-α-diazo ketones, which are themselves prepared by silylation of the corresponding diazo ketones. The mechanism of the annulation reaction is proposed to involve the formation of a 2,3-bis(silyl)cyclopropanone, which is in equilibrium with an oxyallylic cation. Electrocyclic closure of this intermediate forms the new cyclopentenone ring.
