By Eli Breuer

ISBN-10: 0470772190

ISBN-13: 9780470772195

ISBN-10: 0471917095

ISBN-13: 9780471917090

The second one quantity during this new sequence of updates comprises chapters at the chemistry of amino-, nitroso-, and nitro- compounds, supported by way of chapters from the 1969 quantity and the 1982 complement F. This survey contains an updated evaluate of analysis in nitrones, nitronates, and nitroxides.

Content:
Chapter 1 Nitronic acids and esters (pages 1–138): Arnold T. Nielsen
Chapter 2 Nitrones and nitronic acid derivatives: Their constitution and their roles in synthesis (pages 139–244): Eli Breuer
Chapter three Nitrones and nitronic acid derivatives: An replace (pages 245–312): Eli Breuer
Chapter four Nitroxides (pages 313–370): Hans Gunter Aurich
Chapter five Appendix to ‘Nitroxides’ (pages 371–399): Hans Gunter Aurich

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Additional resources for Nitrones, Nitronates and Nitroxides (1989)

Sample text

P. ) a t 25'0 Ref. p. p. ) at 250a Ref. H & =C OD aN0,, CGH, -C=NOzH I (CH,),o L C H z Qp'' e NOZH NOZH (C6Hr),C=NO,H 2-ClC6H4(4-BrC6H,)CHC (CH,)=NO,H 33 27 (continued) Arnold T. p. ) at 250a 4-20 h >6 months > 6 months 4-20 h 4-20 h 8 days 4-20 h Ref. 27 27 21 27 27 27 27 several weeks 205 5 Approximate time for undiluted sample to liquefy or exhibit evident decomposition. of the sample is reported to decompose during the distillation. l). Thus, the conversion of nitronic esters to nitronic acids appears to be a reaction of limited scope and utility, particularly since most esters are prepared from nitronate salts.

The mechanism C6H5CH=N0,H + Cl, C,H,CHClNO, + HC1 (51) involves addition of halogen to a nitronate anion (equation 52). OH R' \C=N' R' \ RS/c=N% rd R' 0- +H+ 'c=N{' Kb RL O \ (52) R' 0- A* - & + X, (or XOH) + \ /I C-NO, + X- (or OH-) RS X X = C1, Br, I Addition of iodine monochloride (IC1) produces the iodo compound, R'R*CINO,, and chloride ion2". I t is to be noted that a-halonitroalkanes are most conveniently prepared by halogenation of nitronate salts. 46 Arnold T. Nielsen Reaction of nitrous acid with nitronic acids and salts yields pseudonitroles ( b l ~ e ) ~ ~ ~ These * ~ ~ pseudonitroles ~ * ~ ~ ~ - derived ~ ~ ~ .

Certain other aryl nitronate salts behave ~ i m i l a r l y ~ ~ ~ ~ ~ ” . p-UrC H C-NO,-Na+ N a O H , aq. 150- 160” p-RrC6H4CH= CHC6H4Rr-p (90) 5-6 h 4~ (: S (85) (84) 70-80°, 3. Reactions of a-halonitronic acids The a-halonitronic acids, R C (X)=NO ,H ( X = halogen), are somewhat unique in the ease with which they undergo displacement of halide ion by various nucleophiles. Reactions of these substances are believed to occur with a nitronic acid, rather than a nitronate intermediate. 320. a-Halonitronic acids are reactive and attempts to isolate them have failed32.

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Nitrones, Nitronates and Nitroxides (1989) by Eli Breuer


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