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Ethanolysis of tertiary 9-chloro-bicyclo(3.3.1)nonanes

โœ Scribed by L. Baiocchi; M. Giannangeli; G. Palazzo

Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
171 KB
Volume
11
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The solvolysis rates of a series of tertiary&-aryl-substituted cycloalkyl chlorides were recently determined (1). This series did not include 9-substituted-bicyclo(3.3.1)nonanes, the only available data being on the acetolysis of secondary tosylates, from which many rearranged products are obtained (2,s). We have therefore synthesized the tertiary chlorides Ia, b, c, d and studied their ethanolysis. 9-Chloro-9-methyl-bicyclo(3.3.l)nonane Ia (m.p. 130") is readily obtained by heating the corresponding carbinol (m.p. 170") with concentrated hydrogen

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The title compound has been synthesized stereoselectively based on a new methodology for the construction of erythro-1,3-diols. Endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane (11, first isolated by Heemann and Francke in 1976 from Norway spruce attacked by the ambrosia beetle (Tgypodendron Lineatum