219140-91-7Relevant academic research and scientific papers
Catalytic isomerization of 1-alkynyl-2,3-epoxy alcohols to substituted furans: Succinct routes to furanoid fatty acids and difurylmethanes
Marson, Charles M.,Harper, Steven
, p. 9223 - 9231 (1998)
A versatile procedure for the preparation of synthetically valuable 2,5- disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)- catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic α- alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(α hydroxyalkyl)furans 4.
