Benzohydroximoyl chlorides have been examined for the first time and are shown to react (as the conjugate ion) > 1 07-fold more slowly than the corresponding (2)benzohydroximoyl chloride anions. This large rate difference is attributed to the favourable antiperiplanar lone pair on the adjacent nitrogen which facilitates CIloss from the (2) -substrate. The (2) -benzohydroximoyl chlorides were formed by direct chlorination of ( E )or ( Z ) -benzaldoximes while the ( E ) -chlorides were formed by acylation of these (Z) -isomers, photoisomerisation and separation, and then subsequent deacylation in situ.
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