Syntheses of 2-oxabicyclohexadec-1(6)-ene from cyclododecanone

Article abstract of DOI:10.1007/BF00699833

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 cyclododecanobe with 1-bromo-3-tert-butoxypropane followed by removal of the protecting tert-butyl group and elimination of water. - 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(16)-ene, 2-(3-chloropropen-3-yl)cyclododecanone, 2-(3-benzyloxypropyl)cyclododecanone, 2-(3-tert-butoxypropyl)cyclododecanone, 2-(3-acetoxypropyl)cyclododecanone, 2-(3-hydroxypropyl)cyclododecanone.