Cyclodecanone 2 hydroxy

Thioacetals, prepared from the corresponding ketones, have also been reduced to alkenes using moderately active Raney nickel as the desulfurization agent (Scheme 37). This form of Raney nickel does not reduce the newly formed alkene or react with other isolated carbon-carbon double bonds. Note that under these conditions the saturated hydrocarbon often observed in Raney nickel desulfurizations is not formed. Similar conditions have been used for the conversion of cyclodecanone to cyclodecene. While thioacetals have also served as intermediates in the analogous conversion of enones into dienes, a mixture of diene products is obtained. For instance, dithiane generation from 17p-hydroxy-A -androsten-3-one, followed by desulfurization affords a 4 1 mixture of 17P-hydroxy-A -androstadiene and 17P-hy-droxy-A -androstadiene, respectively. ... 

Cupric acetate is also used for oxidations of acyloins. Diphenylacetoin is converted almost quantitatively into dibenzylglyoxal when refluxed with cupric acetate in 70% acetic acid for 7 min [353]. Sebacoin (2-hydroxy-cyclodecanone) gives sebacil in 88-89% (equation 449) yield [359]. 

The cyclodecanone ring of ( )-3P-hydroxy-5,10-seco-l(10)-cholesten-5-one was shown to adopt an extended crown conformation by an A -ray structure determination of its p-bromobenzoate. In contrast, analysis of the and n.m.r. spectra of its acetate showed two conformations to be present in solution, the major one (85%) corresponding to the extended crown observed in the solid state, and the minor one corresponding to conformation (23). The failure of force-field calculations to reproduce the energy differences between different conformations was attributed to a transannular interaction between the double bond and the carbonyl group. The observed conformations were used to rationalize the stereochemistry of several reactions of these seco-steroids. ... 

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