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Competition between substitution (SN2), elimination (E2) and addition elimination (AE) reactions in the gas Phase

✍ Scribed by J. Haib; D. Stahl

Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 671 KB
Volume: 27
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210270406

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✦ Synopsis

The competition between substitution (sN2), elimination (E2) and additiorrelimination (AE) reactions in the gas phase has been studied by using OH-and NH,as nucleophiles reacting with esters of acetylenedicarboxylic acid of general formula RO(O)CCZCC(O)OR'. By selectively varying R and R' it was possible to show that the E2 reaction predominates over SN2 and that the relative contributions of the three reactions with OH-follow the decreasing order AE > E2 > SN2, whereas for NH,-it is E2 > A E > SN2. The E2 reaction is discussed in terms of substituent effects, relative acidity of the different phydrogens and geometry of the transition state. For the AE reaction a leaving group order for this class of compounds was established.

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