Journal of the Chemical Society. Perkin transactions I p. 2395 - 2406 (1993)
Update date:2022-08-04
Topics:
Cornwall, Philip
Dell, Colin P.
Knight, David W.
Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290 deg C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers.Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions.The corresponding 3-furyl analogues 56 and 59 display similar reactivities.
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