Substitution reactions under NH3 chemical ionization conditions in cis-/trans-1,2-dihydroxybenzosuberans |
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Authors: | K. P. Madhusudanan Mohan Prasad Shri Nivas Rastogi D. Fraisse |
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Abstract: | The nucleophilic substitution reaction under NH3 chemical ionization (CI) conditions in cis- and trans-1,2-dihydroxybenzosuberans (1–4) has been studied with the help of ND3 CI and metastable data. The results indicate that in the parent diols 1 (cis) and 2 (trans), the substitution ion [MsH]+, is produced mainly by the loss of H2O from the [MNH4]+ ion (SNi reaction) while in their 7-methoxy derivatives 3 and 4, the ion-molecule reaction between [M? OH]+ and NH3 seems to be the major pathway for the formation of [MsH]+. The substitution ion from 1 and 2 and the [MH]+ ion from trans-1-amino-2-hydroxybenzosuberan give similar collision-induced dissociation mass-analysed ion kinetic energy spectra. Interestingly, their diacetates do not undergo the substitution reaction. |
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