Kinetics of solvolysis of 1-acetyl-4-(1-ethoxycarbonyl-1-cyano) methylene-1,4-dihydroquinoline in undried DMSO-d6· formation of Acetic Anhydride as an intermediate
✍ Scribed by Leroy H. Klemm; Jennifer J. Lu; Richard A. Klemm
- Book ID
- 102443450
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 367 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0538-8066
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✦ Synopsis
The kinetics of solvolysis of the title compound (QAc) in undried DMSO-ds to give 4-(1ethoxycarbonyl-l-cyano)methylquinoline (QH) and HOAc a t ambient temperature were investigated by 'H nmr spectrometry. With a limited excess of water the solvolysis follows a three-step process of QAc + HzO 3 QH + HOAc, QAc + HOAc 2 QH + AcpO, and AczO + H20 3 2 HOAc, where kz > kl and k 3 < kl. Addition of pyridine-%5 to the reaction mixture markedly catalyzes the overall solvolysis, while addition of CF3C02D to the reaction mixture simplifies the kinetics to pseudo first-order in [QAc] with k = 4.3 x min-I.