The Chichibabin Reaction of Purines with Potassium amide in Liquid Ammonia

N.J. Kos, H.C. van der Plas, B. van Veldhuizen

Research output: Contribution to journalArticleAcademicpeer-review

22 Citations (Scopus)

Abstract

Reaction of purine and 2-methyl- and 8-methylpurine with potassium amide in liquid ammonia leads to the formation of adenine and 2-methyl- and 8-methyladenine, respectively. 6-Methyl- and 6,8-di-tert-butylpurine do not react. It was proven by applying 15N-labeled potassium amide that the amination reactions do not involve opening of the pyrimidine ring. Low temperature NMR spectroscopy showed that in solutions of purine and 2-methylpurine in potassium amide-liquid ammonia an anionic σ complex at position 6 is formed. 8-Methylpurine on the contrary only showed the presence of a monoanion and a dianion.
Original languageEnglish
Pages (from-to)3140-3143
JournalJournal of Organic Chemistry
Volume44
Issue number18
Publication statusPublished - 1979

Fingerprint Dive into the research topics of 'The Chichibabin Reaction of Purines with Potassium amide in Liquid Ammonia'. Together they form a unique fingerprint.

Cite this