TY - JOUR
T1 - Mass spectral hydrogen rearrangements of 1,1′‐bicycloalkyldiols under electron impact
AU - Deutsch, Joseph
AU - Chriki, Miriam
PY - 1979/9
Y1 - 1979/9
N2 - 1,1′‐Bicycloalkyl‐2,2′‐diols (mixtures of stereoisomers) and 1,1′‐diols on electron impact give rise to strong peaks equivalent to [M‐1]+ions, corresponding to cycloalkenone fragments and obviously involving hydrogen atom migrations. Deuterium labelling and substitution techniques reveal the operation of different rearrangement mechanisms for the two series of isomeric compounds. Thus, in the 1,1′‐bicycloalkyl‐2,2′‐diols a ring hydrogen atom is involved in the rearrangement, whereas in the 1,1′‐bicycloalkyl‐1,1′‐diols (pinacols) the hydroxylic hydrogen atoms migrate.
AB - 1,1′‐Bicycloalkyl‐2,2′‐diols (mixtures of stereoisomers) and 1,1′‐diols on electron impact give rise to strong peaks equivalent to [M‐1]+ions, corresponding to cycloalkenone fragments and obviously involving hydrogen atom migrations. Deuterium labelling and substitution techniques reveal the operation of different rearrangement mechanisms for the two series of isomeric compounds. Thus, in the 1,1′‐bicycloalkyl‐2,2′‐diols a ring hydrogen atom is involved in the rearrangement, whereas in the 1,1′‐bicycloalkyl‐1,1′‐diols (pinacols) the hydroxylic hydrogen atoms migrate.
UR - http://www.scopus.com/inward/record.url?scp=84986947144&partnerID=8YFLogxK
U2 - 10.1002/oms.1210140905
DO - 10.1002/oms.1210140905
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AN - SCOPUS:84986947144
SN - 0030-493X
VL - 14
SP - 482
EP - 484
JO - Journal of Mass Spectrometry
JF - Journal of Mass Spectrometry
IS - 9
ER -