Solvolyis reactions of perfluoro-5-aza-4-nonene, C3 F7-CF=N-C4F9

A. R. Siedle; Robert J. Webb; R. A. Newmark; Myles Brostrom; David A. Weil; Kristin Erickson; Fred E. Behr; Victor G. Young

doi:10.1016/S0022-1139(03)00084-8

Solvolyis reactions of perfluoro-5-aza-4-nonene, C₃ F₇-CF=N-C₄F₉

A. R. Siedle, Robert J. Webb, R. A. Newmark, Myles Brostrom, David A. Weil, Kristin Erickson, Fred E. Behr, Victor G. Young

Chemistry (Twin Cities)

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

11 Scopus citations

Abstract

Hydrolysis of the imine perfluoro-5-aza-4-nonene, C₃ F₇-CF=N-C₄F₉, in ether was studied by several spectroscopic techniques including ¹⁷O NMR. The initial product is C₃F₇ -CO-NH-C₄F₉ which is converted to (C₃ F₇CO)₂NH and then to C₃F₇ CONH₂ and C₃F₇CO₂H. Solvolysis in liquid ammonia afforded the amidine C₃ F₇-C(=NH)NH₂. Reaction with hydrazine produced 3,5-bis(heptafluoropropyl)-1,2,4-triazole whose crystal structure is reported.

Original language	English (US)
Pages (from-to)	175-182
Number of pages	8
Journal	Journal of Fluorine Chemistry
Volume	122
Issue number	2
DOIs	https://doi.org/10.1016/S0022-1139(03)00084-8
State	Published - Aug 1 2003

Keywords

3,5-bis(Heptafluoropropyl)-1,2,4-triazole
Heptafluorobutyramide
Heptafluorobutyrimide
O NMR
Perfluoro-5-aza-4-nonene
Solvolysis

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10.1016/S0022-1139(03)00084-8

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@article{c37eb1be619846e78d324b0b83243bca,

title = "Solvolyis reactions of perfluoro-5-aza-4-nonene, C3 F7-CF=N-C4F9",

abstract = "Hydrolysis of the imine perfluoro-5-aza-4-nonene, C3 F7-CF=N-C4F9, in ether was studied by several spectroscopic techniques including 17O NMR. The initial product is C3F7 -CO-NH-C4F9 which is converted to (C3 F7CO)2NH and then to C3F7 CONH2 and C3F7CO2H. Solvolysis in liquid ammonia afforded the amidine C3 F7-C(=NH)NH2. Reaction with hydrazine produced 3,5-bis(heptafluoropropyl)-1,2,4-triazole whose crystal structure is reported.",

keywords = "3,5-bis(Heptafluoropropyl)-1,2,4-triazole, Heptafluorobutyramide, Heptafluorobutyrimide, O NMR, Perfluoro-5-aza-4-nonene, Solvolysis",

author = "Siedle, {A. R.} and Webb, {Robert J.} and Newmark, {R. A.} and Myles Brostrom and Weil, {David A.} and Kristin Erickson and Behr, {Fred E.} and Young, {Victor G.}",

year = "2003",

month = aug,

day = "1",

doi = "10.1016/S0022-1139(03)00084-8",

language = "English (US)",

volume = "122",

pages = "175--182",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

number = "2",

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TY - JOUR

T1 - Solvolyis reactions of perfluoro-5-aza-4-nonene, C3 F7-CF=N-C4F9

AU - Siedle, A. R.

AU - Webb, Robert J.

AU - Newmark, R. A.

AU - Brostrom, Myles

AU - Weil, David A.

AU - Erickson, Kristin

AU - Behr, Fred E.

AU - Young, Victor G.

PY - 2003/8/1

Y1 - 2003/8/1

N2 - Hydrolysis of the imine perfluoro-5-aza-4-nonene, C3 F7-CF=N-C4F9, in ether was studied by several spectroscopic techniques including 17O NMR. The initial product is C3F7 -CO-NH-C4F9 which is converted to (C3 F7CO)2NH and then to C3F7 CONH2 and C3F7CO2H. Solvolysis in liquid ammonia afforded the amidine C3 F7-C(=NH)NH2. Reaction with hydrazine produced 3,5-bis(heptafluoropropyl)-1,2,4-triazole whose crystal structure is reported.

AB - Hydrolysis of the imine perfluoro-5-aza-4-nonene, C3 F7-CF=N-C4F9, in ether was studied by several spectroscopic techniques including 17O NMR. The initial product is C3F7 -CO-NH-C4F9 which is converted to (C3 F7CO)2NH and then to C3F7 CONH2 and C3F7CO2H. Solvolysis in liquid ammonia afforded the amidine C3 F7-C(=NH)NH2. Reaction with hydrazine produced 3,5-bis(heptafluoropropyl)-1,2,4-triazole whose crystal structure is reported.

KW - 3,5-bis(Heptafluoropropyl)-1,2,4-triazole

KW - Heptafluorobutyramide

KW - Heptafluorobutyrimide

KW - O NMR

KW - Perfluoro-5-aza-4-nonene

KW - Solvolysis

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U2 - 10.1016/S0022-1139(03)00084-8

DO - 10.1016/S0022-1139(03)00084-8

M3 - Article

AN - SCOPUS:0042804973

SN - 0022-1139

VL - 122

SP - 175

EP - 182

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 2

ER -