ACID CLEAVAGE OF HUMULENE 9,10-EPOXIDE. ANOMALOUS PRODUCTS AND EFFECTS OF STRAIN ON THE REACTION COURSE
- 5 March 1981
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 10 (3) , 351-354
- https://doi.org/10.1246/cl.1981.351
Abstract
Summary On treatment of humulene 9,10-epoxide with BF3·OEt2 in AcOH, seemingly anomalous products 6-acetoxy-7-hydroxy-2,9-humuladiene and 6-acetoxy-2,7(13),9-humulatriene were obtained together with known compounds 2,9-diacetoxy-1,5,8,8-tetramethylbicyclo[8,1,0]undec-5-ene, 9-acetoxy-1,5,8,8-tetramethyltricyclo[8,1,0,02,6] undec-4ene and -5ene. The reaction course was well explained by the strain energy of four possible intermediates expected at the first stage of the transannular reaction.This publication has 7 references indexed in Scilit:
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