- N,N′-Dichloro bis(2,4,6-trichlorophenyl)urea (CC-2): an efficient reagent for the synthesis of α-chloro-nitroso compounds
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A simple, efficient, rapid, and mild method for the synthesis of α-chloro-nitroso compounds is described using bis(2,4,6-trichlorophenyl)urea (CC-2).
- Gupta,Acharya,Pardasani,Dubey
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p. 767 - 770
(2007/10/03)
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- Formation of O-allyl oximes by reaction of allylzinc reagents with α-chloronitroso compounds
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The reaction of α-chloronitrosocyclohexane with allyl-zinc reagents in THF selectively provides O-allylcyclohexanone oximes in very good yields in an ene type reaction followed by zinc halide elimination. N-Allyl hydroxylamines are formed as minor product
- Filip, Sorin V.,Sewald, Norbert
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p. 3565 - 3570
(2007/10/03)
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- C-Nitroso compunds. Part XXXVII. The reactivity of α-chloronitroso compounds towards organoaluminium reagents
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With sterically unhindered and certain moderately hindered α-chloronitroso compounds 1 trimethylaluminium at low temperature gives, via complexes 2 and 3, the methyl nitrones 4 (Scheme 1).Several intermediate complexes 3 lose methane upon heating and rearrange to α-chloroimines 5 (Scheme 2), the structure of which is determined by that of the precursors (E- or Z-geometry; cf.Scheme 6).More sterically hindered α-chloronitroso compounds containing quaternary carbon undergo C-C rupture when treated with trimethylaluminium, thus forming hydroxamic acid chlorides, formally HCl adducts of nitrile oxides (cf. 8j in Scheme 3; 8k in Scheme 4).In the latter case, subsequent reactions lead to overall ring enlargement, i. e. formation of the seven-membered cyclic oxime 12.With triethylaluminium and triisobutylaluminium, α-chloronitroso compounds are mainly reduced to oximes and the isomeric amides (Scheme 7).
- Lub, J.,Beekes, M. L.,Boer, Th. J. de
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