Reaksi Hammick

Reaksi Hammick, berasal dari nama penemunya Dalziel Hammick, adalah reaksi kimia dekarboksilasi termal asam α-pikolinat dengan keberadaan senyawa karbonil, membentuk 2-piridil-karbinol.[1][2][3]

The Hammick reaction
The Hammick reaction

Dengan menggunakan p-simena sebagai pelarut, telah ditunjukkan bahwa ia akan meningkatkan rendemen reaksi.[4]

Mekanisme

Seketika pemanasan asam α-pikolinat, ia akan berdekarboksilasi membentuk zwiterion (2). Dengan keberadaan elektrofil seperti aldehida, zwiterion akan bereaksi dengan karbonil. Setelah transfer proton, karbinol (4) yang diinginkan terbentuk.

The mechanism of the Hammick reaction
The mechanism of the Hammick reaction

Referensi

  1. ^ Dyson, P.; Hammick, D. L. (1937). "362. Experiments on the mechanism of decarboxylation. Part I. Decomposition of quinaldinic and isoquinaldinic acids in the presence of compounds containing carbonyl groups". J. Chem. Soc.: 1724. doi:10.1039/jr9370001724. Pemeliharaan CS1: Banyak nama: authors list (link)
  2. ^ Hammick, D. L.; Dyson, P. (1939). "172. The mechanism of decarboxylation. Part II. The production of cyanide-like ions from α-picolinic, quinaldinic, and isoquinaldinic acids". J. Chem. Soc.: 809. doi:10.1039/jr9390000809. Pemeliharaan CS1: Banyak nama: authors list (link)
  3. ^ Brown, E. V.; Shambhu, M. B. (1971). "Hammick reaction of methoxypyridine-2-carboxylic acids with benzaldehyde. Preparation of methoxy-2-pyridyl phenyl ketones". J. Org. Chem. 36: 2002. doi:10.1021/jo00813a034. Pemeliharaan CS1: Banyak nama: authors list (link)
  4. ^ Sperber, N.; Papa, D.; Schwenk, E.; Sherlock, M. (1949). "Pyridyl-Substituted Alkamine Ethers as Antihistaminic Agents". J. Am. Chem. Soc. 71: 887. doi:10.1021/ja01171a034. Pemeliharaan CS1: Banyak nama: authors list (link)

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