ISSN:
1573-9171
Keywords:
mass spectrometry
;
chemical ionization
;
tetramethylsilane
;
cyclohexanediols
;
acetates
;
methyl ethers
;
stereochemistry
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The effect of stereochemistry on the mechanism of gas-phase fragmentation of [M+SiMe3]+ ions was studied usingcis- andtrans-1,2- and -1,4-cyclohexanediols, their methyl ethers, and acetates as model compounds. The higher stability of the [M+SiMe3]+ions is characteristic of cis-isomers of all the compounds examined, which is associated with chelation in the case ofcis-cyclohexanediols andcis-methoxycyclohexanols and with the higher reactivity oftrans-isomers due to anchimeric assistance of the methoxy and acetoxy groups. Dehydration is characteristic of the [M+SiMe3]+ ions formed from cyclohexanediols; both hydrogen atoms of the hydroxyl groups take part in the process, thus providing direct evidence of the chelation.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01457777
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