Journal of Organic Chemistry p. 2466 - 2473 (1995)
Update date:2022-08-04
Topics:
Nakatani, Kazuhiko
Takada, Kazunori
Isoe, Sachihiko
The intramolecular cooperative reactions of 1,2-bis(diazoketone)s initiated by the Wolff rearrangement of α-diazoketones have been investigated.Under thermal conditions, 1,2-bis(diazoketone)s are efficiently transformed into 2-cyclopenten-1-one derivatives with complete stereospecificity.Thus, a most extraordinary result is reported, that trans-hydro-2-inden-1-ones (1-3) were synthesized for the first time from trans-1,2-bis(diazoketone)s (5, 11, and 12), respectively.The unprecedented trans-hydroindenone structure was confirmed by X-ray analysis of 3 as well as 1H NMR analysis and was supported by ab initio molecular orbital calculations.The same reactions were also carried out under photochemical conditions and were applied to 1,3-bis(diazoketone)s, giving 2-cyclohexen-1-one derivatives.
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