607357-67-5Relevant academic research and scientific papers
A cyclopropyl-homoallyl rearrangement accompanying the borane-mediated reduction of tosylhydrazones
Kragol, Goran,Benko, Iva,Muharemspahic, Jasmina,Mlinaric-Majerski, Kata
, p. 2622 - 2625 (2003)
The Wolff-Kishner reduction of strained cyclopropyl ketones 9-oxo-2,8-didehydronoradamantane (1) and 5-oxo-2,4-didehydrobrendane (5) proceeds without rearrangement, while the borane-mediated reduction of the corresponding tosylhydrazones 1a and 5a affords the rearranged products tricyclo[4.2.1.03.8]non-4-ene (3) and 4-brendene (7), respectively. Rearrangement also occurs during the reduction of the less-strained tosylhydrazones 8a and 10a derived from cyclopropyl methyl ketone (8) and bicyclo[4.1.0]heptan-2-one (10). The results obtained in experiments with deuterated reagents support a concerted mechanism of diazene decomposition/cyclopropyl-homoallyl rearrangement. This rearrangement offers a great possibility for the preparation of new polycyclic molecules and, moreover, is a convenient method for regiospecific isotopic labeling using deuterated reagents. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
