An efficient preparation of vinamidinium hexafluorophosphate salts

Authors
Davies, IW Marcoux, JF Wu, J Palucki, M Corley, EG Robbins, MA Tsou, N Ball, RG Dormer, P Larsen, RD Reider, PJ
Citation
Iw. Davies et al., An efficient preparation of vinamidinium hexafluorophosphate salts, J ORG CHEM, 65(15), 2000, pp. 4571-4574
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
15
Year of publication
2000
Pages
4571 - 4574
Database
ISI
SICI code
0022-3263(20000728)65:15<4571:AEPOVH>2.0.ZU;2-Z
Abstract
Substituted acetic acids or acetyl chlorides react with phosphorus oxychlor ide in DMF to yield the vinamidinium salts 3a-j in moderate to excellent re crystallized yields (28-90%). The cations are conveniently isolated as thei r hexafluorophosphate salts, which are easily handled nonhygroscopic solids . The nitro compound 31 is prepared in 91% yield by nitration of the parent vinamidinium 3k. The X-ray crystal structure is reported for the 2-phenyl isomer 3e and displays minimal overlap of the two pi-systems.