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Tandem Michael reaction. Synthesis of bridged diketones

Kasturi, TR and Pragnacharyulu, PVP and Reddy, Amrutha P (1991) Tandem Michael reaction. Synthesis of bridged diketones. In: Journal of Organic Chemistry, 56 (19). pp. 5564-5566.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00019a018


Addition of NaOMe, NaOEt, or NaOPr(i) to dispironaphthalenone 1 resulted in the formation of diketones 4a-c and 5a-c. The structure assigned to 4a was confirmed by conversion to the known hemiacetal 3. Similar addition of carbon nucleophiles like diethyl malonate, dimethyl malonate, methyl cyanoacetate, and ethyl cyanoacetate afforded diketones 4d-g. Formation of these compounds has been rationalized.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Keywords: Dispiro(Naphthalene-1,2'(1'h)-Naphtho<2,1-B>Pyran-3',1''-Naphthalene)-2(1h),2''.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 07 Dec 2010 08:37
Last Modified: 07 Dec 2010 08:37
URI: http://eprints.iisc.ac.in/id/eprint/34219

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