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Substitution reactions under NH 3 chemical ionization conditions in cis ‐/ trans ‐1,2‐dihydroxybenzosuberans
Author(s) -
Madhusudanan K. P.,
Prasad Mohan,
Rastogi Shri Nivas,
Fraisse D.
Publication year - 1985
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210201107
Subject(s) - chemistry , nucleophilic substitution , ion , substitution reaction , dissociation (chemistry) , ionization , molecule , medicinal chemistry , mass spectrum , chemical ionization , electron ionization , organic chemistry
The nucleophilic substitution reaction under NH 3 chemical ionization (CI) conditions in cis ‐ and trans ‐1,2‐dihydroxybenzosuberans (1–4) has been studied with the help of ND 3 CI and metastable data. The results indicate that in the parent diols 1 ( cis ) and 2 ( trans ), the substitution ion [M s H] + , is produced mainly by the loss of H 2 O from the [MNH 4 ] + ion (S N i reaction) while in their 7‐methoxy derivatives 3 and 4, the ion‐molecule reaction between [MOH] + and NH 3 seems to be the major pathway for the formation of [M s H] + . 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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