How nucleophilic are diazo compounds?

…, M Hartnagel, C Schlierf, H Mayr

Index: Bug, Thorsten; Hartnagel, Manfred; Schlierf, Clemens; Mayr, Herbert Chemistry - A European Journal, 2003 , vol. 9, # 17 p. 4068 - 4076

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Citation Number: 63

Abstract

Abstract The kinetics of the reactions of benzhydryl cations with eight diazo compounds 1 a– g were investigated photometrically in dichloromethane. The nucleophilicity parameters N and slope parameters s of these diazo compounds were derived from the equation log k (20 C)= s (E+N) and compared with the nucleophilicities of other π systems (alkenes, arenes, silyl enol ethers, silyl ketene acetals). It is shown that the nucleophilic reactivities of diazo ...