90690-88-3Relevant academic research and scientific papers
A Clear Demonstration of the Stereoelectronic Effect of Nitrogen in Chloride Ion loss by (E)- and (Z)-Hydroximoyl Chlorides
Hegarty, Anthony F.,Mullane, Maria
, p. 995 - 1002 (2007/10/02)
(E)-Benzohydroximoyl chlorides have been examined for the first time and are shown to react (as the conjugate ion) > 10E7-fold more slowly than the corresponding (Z)-benzohydroximoyl chloride anions.This large rate difference is attributed to the favourab
Stereospecific Bimolecular Displacement at a Carbon-Nitrogen Double Bond leading to Open Chain Imidoyl Azides
Hegarty, Anthony F.,Mullane, Maria
, p. 913 (2007/10/02)
Use of the 'azide trap' for a cis lone pair on nitrogen shows that the Z-halides (1) undergo retention and the E-halides (2) inversion of configuration on reaction with azide ion.
Large Stereoelectronic Effect in 1,3-Dehydrohalogenation to form a 1,3-Dipole
Hegarty, Anthony F.,Mullane, Maria
, p. 229 - 230 (2007/10/02)
The E-hydroximidoyl chloride (5), prepared on photoisomerisation of (1) to (2) and by subsequent hydrolysis, is shown to lose HCl to give benzonitrile oxide 6*107 fold slower than the Z-isomer (3).
