Cyclodecanone synthesis

Regio- and stereospecific 1,3-cycloaddition of di-tert-butylated acyl nitrone (548), generated in situ from (547), with Z-2-cyclodecanone and subsequent aromatization is the key step in the synthesis of biomimetic pyridomacrolidin... 

If the moeity adding to the aryne carries a suitably placed electrophilic center, cyclization with the initially formed anion can occur as observed in the synthesis of dibenzothiophene (60).92 Of wider synthetic import in this context is enolate addition to arynes. Here, after the initial ring closure many types of products can be formed (Scheme ll).35 However, with some substrates, a particular reaction course can predominate 93 94 for example, reaction of cyclodecanone with bromobenzene provides an efficient method for benzo-annulation and ring expansion. Similarly, high yields of benzocyclobutenols can be obtained from the monoketals of ot-diketones.9s... 

Show a synthesis of nylon 10 starting from cyclodecanone ... 

The synthesis of 2-HYDROXYMETHYL-2-CYCLOPENTENONE from cyclopentenone illustrates a general strategy and method for the synthesis of an effective latent synthon of an a-ketovinyl anion. The synthesis of CYCLODODECYL MERCAPTAN from cyclodecanone provides a method for the preparation of secondary or hindered mer-captans which cannot be prepared by traditional displacement reactions. 

When treated with HI in refluxing acetic acid, a-diketones and a-ketols are reduced to satd. ketones. This provides a general ketone synthesis, which in certain cases may be used to shift a carbonyl group to an adjacent position.— E Crude sebacil or sebacoin dissolved in glacial acetic acid, and refluxed 2-2.5 hrs. with 47% HI cyclodecanone. Y 80% from sebacil, 70% from sebacoin. F. e. s. W. Reusch and R. LeMahieu, Am. Soc. 86, 3068 (1964) cf. Steroids 5, 109 (1965). 

Improved conditions have been found for the synthesis of cycloalkynones by Eschenmoser fragmentation of bicyclic epoxy-ketones. Various cyclodecene derivatives have been prepared from the Diels-Alder adduct of cyclo-octyne and furan-3,4-dicarboxylates, ° and some simple cyclodecanones have been obtained from 9-decalinols by radical-induced ring cleavage. ... 

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