Synthesis and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups
Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R F O) 2 P(O)NHR (R = CH 2 CH 2 CH 3 , (CH 2 ) 3 CH 3 , (CH 2 ) 4 -CH 3 , CH(CH 3 ) 2 , C 6 H 11 , CH 2 CH 2 -C 6 H 5 , CH 2 -C 6 H 5 or C 6 H 5 ; R F = CH 2 CF 3 , CH 2 C 2 F 5 or CH 2 CH 2 C 6 F 13 ) were...
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| Published in: | Synthetic communications Vol. 54; no. 15; pp. 1273 - 1283 |
|---|---|
| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Philadelphia
Taylor & Francis
02-08-2024
Taylor & Francis Ltd Taylor & Francis: STM, Behavioural Science and Public Health Titles |
| Subjects: | |
| Online Access: | Get full text |
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| Summary: | Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R
F
O)
2
P(O)NHR (R = CH
2
CH
2
CH
3
, (CH
2
)
3
CH
3
, (CH
2
)
4
-CH
3
, CH(CH
3
)
2
, C
6
H
11
, CH
2
CH
2
-C
6
H
5
, CH
2
-C
6
H
5
or C
6
H
5
; R
F
= CH
2
CF
3
, CH
2
C
2
F
5
or CH
2
CH
2
C
6
F
13
) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H
2
O
2.
This method was chosen out of various literature common methods, which were thoroughly investigated using
31
P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (
1
H,
13
C,
31
P, and
19
F) NMR, IR, and HRMS techniques. |
|---|---|
| ISSN: | 0039-7911 1532-2432 |
| DOI: | 10.1080/00397911.2024.2382784 |