Substitution Reactions Under NH3 Chemical Ionization Conditions in cis-/trans-1,2-Dihydroxybenzosuberans

Article abstract of DOI:10.1002/oms.1210201107

The nucleophilic substitution reaction under NH3 chemical ionization (CI) conditions in cis- and trans-1,2-dihydroxybenzosuberans (1-4) has benn studied with the help ND3 CI and metastable data.The results indicate that in the parent diols 1 (cis) and 2 (trans), the substitution ion, sH>⁺, is produced mainly by the loss of H2O from the ⁺ ion (S_Ni reaction) while in their 7-methoxy derivatives 3 and 4, the ion-molecule reaction between ⁺ and NH3 seems to be the major pathway for the formation of sH>⁺.The substitution ion from 1 and 2 and the ⁺ 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.