Cydoadditions of Trifluoroacetonitrile Oxide with Olefins and Acetylenes
- 1 August 1984
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 57 (8) , 2184-2187
- https://doi.org/10.1246/bcsj.57.2184
Abstract
The regio- and stereoselectivity of the cydoadditions of trifluoroacetonitrile oxide (1) with olefins and acetylenes were described. The oxide 1, generated in situ from trifluoroacetohydroximoyl bromide etherate in the presence of triethylamine, reacted with various monosubstituted olefins and acetylenes to give exclusively 5-substituted 3-trifluoromethyl-2-isoxazolines and -isoxazoles, respectively, whereas 1 cyclized with 1,2-disubstituted olefins and acetylenes to result in the formation of a mixture of two regioisomeric products. On the other hand, the cycloaddition of 1 with (Z)-β-methylstyrene afforded a mixture consisting of two regioisomeric isoxazolines retaining Z-configuration and one diastereoisomeric isoxazoline.This publication has 10 references indexed in Scilit:
- A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxide precursors)The Journal of Organic Chemistry, 1980
- New histamine and histidine analogs via transformations of the 2-trifluoromethyl groupThe Journal of Organic Chemistry, 1980
- Isoxazole anthelminticsJournal of Medicinal Chemistry, 1977
- 1,3-Dipolar cycloadditions. 76. Concerted nature of 1,3-dipolar cycloadditions and the question of diradical intermediatesThe Journal of Organic Chemistry, 1976
- 1,3‐Dipolare Cycloadditionen, 74. Orientierungsphänomene bei Cycloadditionen aliphatischer und aromatischer Nitriloxide an α,β‐ungesättigte Carbonester2)European Journal of Inorganic Chemistry, 1973
- 1,3‐Dipolare Cycloadditionen, 70. Additionen des Benzonitriloxids an olefinische und acetylenische DipolarophileEuropean Journal of Inorganic Chemistry, 1973
- 1.3‐Dipolare Cycloadditionen, XXX. Substituenteneffekte in den Kernresonanzspektren von 1.3‐Diphenyl‐Δ2‐pyrazolinen und 3‐Phenyl‐Δ2‐isoxazolinenEuropean Journal of Inorganic Chemistry, 1967
- Reactions of perfluoroalkyldiazomethanes—IITetrahedron, 1963
- Reactions of perfluoroalkyldiazomethanes—ITetrahedron, 1963
- The Chemistry of the Perfluoro Acids and Their Derivatives. III. The Perfluoro Aldehydes1Journal of the American Chemical Society, 1952