
TY  - JOUR
A1  - Currie, GJ 
A1  - Stringer, MB 
A1  - Bowie, JH 
A1  - Holmes, JL 
T1  - Collision-Induced Carbanion Rearrangements. The Elimination of Ethene From the 3,3-Dimethylheptan-4-one Enolate Ion
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1987
VL  - 40
IS  - 8
SP  - 1365
EP  - 1373
KW  - 
UR  - https://doi.org/10.1071/CH9871365 
N2  - The mechanisms of formation of the major product ions produced by collision activation of the enolate negative ion of 3,3-dimethylheptan-4-one have been studied by deuterium labelling. H2 loss involves 1,2-elimination from the 6- and 7-positions. Methane elimination is complex involving three competitive rearrangement processes. Ethene loss produces the most abundant fragment ion and occurs by elimination of the C1-C2 ethyl group with concomitant proton transfer from the 1-position. In the case of the enolate ion from CD3CH2CMe2COPr, the expected elimination of C2H2D2 competes with loss of C2H4 from positions 6 and 7. Other decompositions are as follows: loss of C3H8 involves the methyl and ethyl substituents at positions 7, 1 and 2 respectively; loss of C4H8 occurs by two processes, ( i ) successive losses of two C2H4 units (from the 1, 2 then 6, 7 positions), and (ii) loss of CH2=CMe2 (from the 2 and 3 positions); and loss of C5H12 produces Et-C=C-0-.  . 
ER  -

