4883-68-5Relevant articles and documents
ω-Alkenyl α-Nitroalkyl Radicals. Part 3. Radical Chain Reactions of ω-Alkenyl α-Halogenonitroalkanes
Bowman, W. Russell,Brown, David S.,Burns, Catherine A.,Crosby, David
, p. 2083 - 2090 (2007/10/02)
SRN1 reactions between 5-bromo-5-nitrohex-1-ene and the nitronate anions of 2-nitropropane and 5-nitrohex-1-ene failed to give cyclisation of the intermediate α-nitroalkyl radical onto the alkene.Reaction between exo-5-bromo-endo-5-nitro-exo-6-phenylbicyclohept-2-ene 1 and the anion of 2-nitropropane did not undergo an SRN1 reaction and Br+ abstraction gave 2-bromo-2-nitropropane and 5-endo-nitro-exo-6-phenylbicyclohept-2-ene.BNAH reduction of exo-5-bromo-endo-5-nitro-exo-6-phenylbicyclohept-2-ene 1, 6-bromo-6-nitrohept-1-ene, and 1-bromo-1-nitro-2-(prop-2-enyl)cyclohexane gave the corresponding nitroalkanes without any cyclosation of the intermediate α-nitroalkyl radicals.Initial results indicate that an iodine atom transfer methodology provides a possible general method for the cylisation of ω-alkenyl α-nitroalkyl radicals.Cyclisation of intermediate α-nitroalkyl radicals, generated by photolysis of 1-(bicyclohept-5-en-endo-2-yl)-2-iodo-2-nitropropane 5a, gave a good yield of two diastereomeric tricyclic iodonitro compounds 6a and 7a.Photolysis of 1-(bicyclohept-5-en-endo-2-yl)-2-iodo-2-nitroethane 5b and 2-(but-3-enyl)-1-iodo-1-nitrocyclohexane 11 also gave the expected products from 5-exo cyclisation of the intermediate α-nitroalkyl radicals.The tricyclic iodonitro compound 6a was synthesised from the corresponding endo-methanesulfonate 15, the structure of which was determined by X-ray crystallography.
2 plus 2.
Borisenko,Nikulin,Wolfe,Zefirov,Zyk
, p. 1074 - 1079 (2007/10/18)
The reactions of AcONO//2 with the cyclic olefins cyclopentene, cyclohexane, cis-cyclooctene, methylenecyclobutane, and norbornene have been investigated or, in some cases, reinvestigated. Although many products are formed, material balances in the order
