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Studies on the mechanism of the hydrazine reduction reaction: Applications to selected monoethylenic, diethylenic and triethylenic fatty acids of cis configurations
Author(s) -
Ratnayake W. M. N.,
Grossert J. S.,
Ackman R. G.
Publication year - 1990
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02541853
Subject(s) - chemistry , reactivity (psychology) , double bond , hydrazine (antidepressant) , protonation , methylene , medicinal chemistry , stereochemistry , organic chemistry , medicine , ion , alternative medicine , pathology , chromatography
The hydrazine reduction of cis ethylenic bonds has been studied using a number of C 16 , C 18 , and C 20 monoethylenic, C 18 diethylenic, and C 18 plus C 20 triethylenic fatty acids. Relative reduction rates were determined and correlated with the positions of the ethylenic bonds in the fatty acids. The terminal ethylenic bond was the most reactive and among the others, reactivity was greater nearer the ends of the chain than in the center. Also, the ethylenic bonds closer to the carboxyl group showed greater reactivity than those closer to the methyl end of the chain. Differences in reactivity among the centrally located double bonds were not significant. These reactivity trends are consistent with a mechanism involving protonated diimide as an intermediate in the reduction process. In diethylenic fatty acids, the non‐methylene‐interrupted dienes showed slightly lower reactivity than the methylene‐interrupted counterparts, which indicated that both the position of ethylenic bonds and the relative distance between two ethylenic bonds in the diene influence the rate of reaction. The information obtained from the rate studies should be useful for predicting the product distribution from partial hydrazine reductions of long‐chain polyethylenic compounds.