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Synthese von Tetradecano-14-lacton durch Ringerweiterung

✍ Scribed by Kalina Kostova; Manfred Hesse

Publisher
John Wiley and Sons
Year
1995
Tongue
German
Weight
437 KB
Volume
78
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthesis of Tetradecano‐14‐lactone by Ring Enlargement

The aldehyde 3, prepared by ozonolysis of 2‐allyl‐2‐nitrocyclododecanone, gave the ring‐enlargement product 5(85%) by treatment with (i‐Bu)~2~AlH. Its transformation to the tetradecano‐14‐lactone (8) via the aldol ester 6 and other routes (best is reduction with Bu~3~SnH, AlBN, toluene) was difficult. Remarkable is the smooth denitrification of 3 (loss of HNO~2~) to the conjugated dione 4 by chromatography on silica gel or base treatment.

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