Acid-promoted rearrangements involving transannular ether oxygen participation

LA Paquette, RW Begland…

Index: Paquette,L.A. et al. Journal of the American Chemical Society, 1968 , vol. 90, p. 6148 - 6153

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Citation Number: 14

Abstract

Abstract: When 7, 8-dihydro-2H-oxocin-3 (4H)-one (14) was heated with hydrochloric acid for several minutes, transannular rearrangement involving participation of ether oxygen was encountered and 5-(3-chloropropyl) dihydro-3 (2H)-furanone (13a) was isolated in good yield. Exposure of 14 to hydrobromic acid gave rise to the corresponding bromide (13b). Under similar conditions, 7, 8-dihydro-5-phenyl-2H-oxocin-3 (4H)-one (22) and 5-phenyl- ...