Preparation and novel reduction reactions of vinamidinium salts

I. W. Davies, M. Taylor, J. F. Marcoux, J. Wu, P. G. Dormer, D. Hughes, P. J. Reider

Research output: Contribution to journalArticlepeer-review

29 Scopus citations


Substituted acetic acids and formamides react in the presence of phosphorus oxychloride to yield the vinamidinium hexafluorophosphate salts 5a-d, 6a-d, and 7 in moderate to good unoptimized recrystallized yields, (40-67%) as easily handled nonhygroscopic solids. The 1,3-differentially substituted vinamidinium salts 8 was prepared by amine exchange in 81% yield as are the cyclic diazapinium salts 9 and 19 in >76% yield. The symmetrical 2-chlorovinamidinium 11 was prepared by displacement of 3 in 71% yield. The 2-chlorovinamidinium salts are cleanly reduced to the parent vinamidinium salts 12-16 using HI or PPh3/pTSA in up to 99% assay yield.

Original languageEnglish (US)
Pages (from-to)251-255
Number of pages5
JournalJournal of Organic Chemistry
Issue number1
StatePublished - Jan 12 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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