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 journalArticle

28 Scopus citations

Abstract

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
Volume66
Issue number1
DOIs
StatePublished - Jan 12 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Preparation and novel reduction reactions of vinamidinium salts'. Together they form a unique fingerprint.

  • Cite this

    Davies, I. W., Taylor, M., Marcoux, J. F., Wu, J., Dormer, P. G., Hughes, D., & Reider, P. J. (2001). Preparation and novel reduction reactions of vinamidinium salts. Journal of Organic Chemistry, 66(1), 251-255. https://doi.org/10.1021/jo005656p