An efficient preparation of vinamidinium hexafluorophosphate salts

Ian W. Davies; Jean Francois Marcoux; Jimmy Wu; Michael Palucki; Edward G. Corley; Michael A. Robbins; Nancy Tsou; Richard G. Ball; Peter Dormer; Robert D. Larsen; Paul J. Reider

doi:10.1021/jo000159u

An efficient preparation of vinamidinium hexafluorophosphate salts

Ian W. Davies
, Jean Francois Marcoux
, Jimmy Wu
, Michael Palucki
, Edward G. Corley
, Michael A. Robbins
, Nancy Tsou
, Richard G. Ball
, Peter Dormer
, Robert D. Larsen
, Paul J. Reider

Research output: Contribution to journal › Article › peer-review

71 Scopus citations

Abstract

Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a-j in moderate to excellent recrystallized yields (28-90%). The cations are conveniently isolated as their 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 π-systems.

Original language	English (US)
Pages (from-to)	4571-4574
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	65
Issue number	15
DOIs	https://doi.org/10.1021/jo000159u
State	Published - Jul 28 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo000159u

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@article{7d1665559dd241e7b08825266584428d,

title = "An efficient preparation of vinamidinium hexafluorophosphate salts",

abstract = "Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a-j in moderate to excellent recrystallized yields (28-90\%). The cations are conveniently isolated as their 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 π-systems.",

author = "Davies, \{Ian W.\} and Marcoux, \{Jean Francois\} and Jimmy Wu and Michael Palucki and Corley, \{Edward G.\} and Robbins, \{Michael A.\} and Nancy Tsou and Ball, \{Richard G.\} and Peter Dormer and Larsen, \{Robert D.\} and Reider, \{Paul J.\}",

year = "2000",

month = jul,

day = "28",

doi = "10.1021/jo000159u",

language = "English (US)",

volume = "65",

pages = "4571--4574",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - An efficient preparation of vinamidinium hexafluorophosphate salts

AU - Davies, Ian W.

AU - Marcoux, Jean Francois

AU - Wu, Jimmy

AU - Palucki, Michael

AU - Corley, Edward G.

AU - Robbins, Michael A.

AU - Tsou, Nancy

AU - Ball, Richard G.

AU - Dormer, Peter

AU - Larsen, Robert D.

AU - Reider, Paul J.

PY - 2000/7/28

Y1 - 2000/7/28

N2 - Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a-j in moderate to excellent recrystallized yields (28-90%). The cations are conveniently isolated as their 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 π-systems.

AB - Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a-j in moderate to excellent recrystallized yields (28-90%). The cations are conveniently isolated as their 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 π-systems.

UR - https://www.scopus.com/pages/publications/0034725734

UR - https://www.scopus.com/pages/publications/0034725734#tab=citedBy

U2 - 10.1021/jo000159u

DO - 10.1021/jo000159u

M3 - Article

C2 - 10959861

AN - SCOPUS:0034725734

SN - 0022-3263

VL - 65

SP - 4571

EP - 4574

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

An efficient preparation of vinamidinium hexafluorophosphate salts

Abstract

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