Abstract
Two methods for the synthesis of 2-oxabicyclo[4.10.0]hexadec-1(6)-ene from cyclododecanone have been suggested. The most convenient method involves the preparation of 2-(3-tert-butoxypropyl)cyclododecanone by phase-transfer catalyzed alkylation of cyclododecanone with l-bromo-3-tert-butoxypropane followed by removal of the protectingtert-butyl group and elimination of water.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 659–661, April, 1994.
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Zakharkin, L.I., Churilova, I.M. Syntheses of 2-oxabicyclo[4.10.0]hexadec-1(6)-ene from cyclododecanone. Russ Chem Bull 43, 608–611 (1994). https://doi.org/10.1007/BF00699833
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DOI: https://doi.org/10.1007/BF00699833
Key words
- cyclododecanone
- phase-transfer catalysis
- alkylation
- 2-(3,3-diethoxypropyl)cyclododecanone
- 2-(3,3-ethylenedioxypropyl)cyclododecanone
- 12-hydroxybicyclo[9.3.1]pentadecane-15-one
- 3-ethoxy-2-oxabicyclo[4.10.0]hexadec-1(6)-ene
- 2-(3-chloropropen-3-yl)cyclododecanone
- 2-(3-benzyloxypropyl)cyclododecanone
- 2-(3-tert-butoxypropyl)cyclododecanone
- 2-(3-acetoxypropyl)cyclododecanone
- 2-(3-hydroxypropyl)cyclododecanone