34889-98-0Relevant academic research and scientific papers
Blocking fluorine substitution in biotransformation of nortricyclanyl N-phenylcarbamates with Beauveria bassiana
Haufe, Guenter,Woelker, Doerthe
, p. 2159 - 2165 (2003)
The biotransformation of tricyclo[2,2,1,02,6]hept-3-yl N-phenylcarbamate (8) by a standard procedure using Beauveria bassiana gave a 7:1 mixture of optically active exo,exo- and exo,endo-5-hydroxytricyclo[2.2.1.02,6]hept-3-yl N-phenylcarbamates 15 and 16 in 19% isolated yield. No ring opening of the three-membered ring was observed. Substitution with a fluorine atom at the 5-endo- or 5-exo-position prevented hydroxylation of any alicyclic position of the molecules, p-hydroxylation of the aromatic ring occurring to a small extent instead. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Chemistry of Dioxiranes. 10. Oxidation of Quadricyclane and Norbornadiene by Dimethyldioxirane
Murray, Robert W.,Pillay, M. Krishna,Jeyaraman, Ramasubba
, p. 3007 - 3011 (2007/10/02)
Treatment of quadricyclane (2) with dimethyldioxirane (1) leads to the formation of exo-norborna-2,5-diene monoepoxide (4), exo,exo-norborna-2,5-diene diepoxide (5), bicyclohex-2-ene-6-endo-carboxaldehyde (6), and exo-2,3-epoxybicyclohexane-6-endo-carboxaldehyde(7).The reaction is believed to involve prior catalyzed isomerization of 2 by 1 to norbornadiene (3) and subsequent conversion of 3 to the observed products.Under suitable conditions 1 reacts with 3 to give 4 and 6 in a 97:3 distribution, respectively.
