Abstract
Two [3+1] fragmentations of the Lewis acid stabilized bicyclo[1.1.0]tetraphosphabutanide Li[Mes*P4⋅ BPh3] (Mes*=2,4,6-tBu3C6H2) are reported. The reactions proceed by extrusion of a P1fragment, induced by either an imidazolium salt or phenylisocyanate, with release of the transient triphosphirene Mes*P3, which was isolated as a dimer and trapped by 1,3-cyclohexadiene as a Diels–Alder adduct. DFT quantum chemical computations were used to delineate the reaction mechanisms. These unprecedented pathways grant access to both P1- and P3-containing organophosphorus compounds in two simple steps from white phosphorus.
| Original language | English |
|---|---|
| Pages (from-to) | 285-290 |
| Number of pages | 6 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2017 |
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Keywords
- anions
- fragmentation
- Lewis acids
- organophosphorus compounds
- phosphorus
Cite this
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Selective [3+1] Fragmentations of P4by “P” Transfer from a Lewis Acid Stabilized [RP4]−Butterfly Anion. / Borger, Jaap E.; Ehlers, Andreas W.; Lutz, Martin; Slootweg, J. Chris; Lammertsma, Koop.
In: Angewandte Chemie - International Edition, Vol. 56, No. 1, 2017, p. 285-290.Research output: Contribution to Journal › Article › Academic › peer-review
TY - JOUR
T1 - Selective [3+1] Fragmentations of P4by “P” Transfer from a Lewis Acid Stabilized [RP4]−Butterfly Anion
AU - Borger, Jaap E.
AU - Ehlers, Andreas W.
AU - Lutz, Martin
AU - Slootweg, J. Chris
AU - Lammertsma, Koop
PY - 2017
Y1 - 2017
N2 - Two [3+1] fragmentations of the Lewis acid stabilized bicyclo[1.1.0]tetraphosphabutanide Li[Mes*P4⋅ BPh3] (Mes*=2,4,6-tBu3C6H2) are reported. The reactions proceed by extrusion of a P1fragment, induced by either an imidazolium salt or phenylisocyanate, with release of the transient triphosphirene Mes*P3, which was isolated as a dimer and trapped by 1,3-cyclohexadiene as a Diels–Alder adduct. DFT quantum chemical computations were used to delineate the reaction mechanisms. These unprecedented pathways grant access to both P1- and P3-containing organophosphorus compounds in two simple steps from white phosphorus.
AB - Two [3+1] fragmentations of the Lewis acid stabilized bicyclo[1.1.0]tetraphosphabutanide Li[Mes*P4⋅ BPh3] (Mes*=2,4,6-tBu3C6H2) are reported. The reactions proceed by extrusion of a P1fragment, induced by either an imidazolium salt or phenylisocyanate, with release of the transient triphosphirene Mes*P3, which was isolated as a dimer and trapped by 1,3-cyclohexadiene as a Diels–Alder adduct. DFT quantum chemical computations were used to delineate the reaction mechanisms. These unprecedented pathways grant access to both P1- and P3-containing organophosphorus compounds in two simple steps from white phosphorus.
KW - anions
KW - fragmentation
KW - Lewis acids
KW - organophosphorus compounds
KW - phosphorus
UR - http://www.scopus.com/inward/record.url?scp=85006515941&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85006515941&partnerID=8YFLogxK
U2 - 10.1002/anie.201607234
DO - 10.1002/anie.201607234
M3 - Article
VL - 56
SP - 285
EP - 290
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1521-3773
IS - 1
ER -