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Nucleophilic attacks on carbon-nitrogen double bonds. Part I. Substitution of diarylimidoyl chlorides with amines in benzene

✍ Scribed by Zvi Rappoport; Rachel Ta-Shma


Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
208 KB
Volume
12
Category
Article
ISSN
0040-4039

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✦ Synopsis


While several substitution meohauisms of 8 leaving group attoohed to a ;CX: bond arelmown,' those at 8 ;c?r-bond were little etudied. The kinetios of the hydrolyeis of the -C(Cl)=lF system was studied only by Ugi* =d that of the -C(X)*-lV-system by Soott end ooworkers.3 Intermediate nitrilium halide ion pairs + (-I$&-X') were suggested, based on the kinetio dependenoe on the nuoleophile and


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## Abstract Substitution reactions of 13 para‐ and meta‐substituted anilines with benzenesulfonyl chloride in varying mole fractions of benzene in propan‐2‐ol have been investigated conductometrically. The second‐order rate constants correlate well with pK~a~ values of anilines and with the Hammett