By Saul Patai
Chapter eight The formation of unsaturated teams via heterolytic fragmentation (pages 653–723): Konrad B. Becker and Cyril A. Grob
Chapter nine Electrophilic additions to carbon–carbon double bonds (pages 725–912): George H. Schmid and Dennis G. Garratt
Chapter 10 The olefin metathesis response (pages 913–964): Nissim Calderon
Chapter eleven Oxidation of C?C and C?N teams (pages 965–1098): P. M. Henry and G. L. Lange
Chapter 12 Transition steel catalysed carbonylation of olefins (pages 1099–1166): John ok. Stille and David E. James
Chapter thirteen Imidines and diamidides (1,3,5?triazapentadienes) (pages 1167–1249): John A. Elvidge and N. R. Barot
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Extra info for Double-Bonded Functional Groups: Volume 2 (1977)
CH,),C-0-C-NHR H,O+ (CH,),C+ b I1 + CO, + RNH, 0 (248) (247) 2 The facile formation of the r-butyl cation (248) as the electrofugal fragment is thekasis for the widespread use of the t-butyl group in the temporary protection of functional groups. Thus, t-butoxycarbonyl derivatives of amines (247) are readily cleaved by acids with the liberation of the amine, CO, and the t-butyl cation (248) which is subsequently converted to isobutene' 15. a ROt + :Cx, (2491 ___* R-0--'C-X (250) - Rf + '6=0+ X- Konrad B.
G. for alkaloids. Thus, P-aminoalcohols containing a nucleofuge on the nitrogen atom, undergo fragmentation to imines in the presence of base (equation 30). The nucleofuge X is frequently chlorine68, because Nchloro amines are readily obtained with N-chlorosuccinimide and other chlorinating agents. + HOCHCH,NHNH(CH,), I Ph - PhCHO + CH,=NH + (CH,),NH (17 8 ) Acid-catalysed fragmentation is illustrated by the reaction of N,Ndimethyl-N'-(2-hydroxy-2-phenylethyl)hydrazinium ion (178), which undergoes N-N bond cleavage69.
D. OH Fragmentation also occurs in the deamination of y-amino alcohols via diazonium ions (l19)31. However. the nucleofugal gr&p may also be an ammonio (120)~'or an azoxy group ( 1 2 1 ) ~ ~ . c I l l I l l HO-C-C-C-X (119) X = + -N=N (120) X = -i(CH3)= (121) X = -N=NR I 0 684 Konrad B. Becker and Cyril A. Grob Many fragmentable compounds of the type 122 are generated in situ by the addition of a nucleophile Y, such as a Grignard reagent or hydroxide, alkoxide and hydride ions, to a ketone or aldehyde bearing a P-nucleofuge (reaction 21)34.