Unusual conversion of perfluoromethylepoxycyclopentane into a linear β-aminovinylketone by C-C bond cleavage

2,3,3,4,4,5,5-Heptafluoro-1-trifluoromethyl-1,2-epoxycyclopentane reacted with 2-isopropyl-acetophenone imine giving 2,3,3,4,4,5,5-heptafluoro-2-trifluoromethyl-1-(2'-isopropylimino-2'-phenylethane) cyclopentan-1-ol, which in its turn underwent an intramolecular rearrangement yielding the linear 4,4,5,5,6,6,7,8,8,8-decafluoro-1-isopropylamino-oct-1-en-3-one, being characterized by X-ray structural analysis (triclinic, P-1, a = 920.5(2), b = 1027.9(3), c = 1127.4(3) pm, alpha = 110.99, beta = 105.68degrees, gamma = 96.75degrees). (C) 2002 Elsevier Science B.V. All rights reserved.