An Iron‐Catalyzed Route to Dewar 1,3,5‐Triphosphabenzene and Subsequent Reactivity
Publication type: Journal Article
Publication date: 2022-08-09
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
35851715
General Chemistry
Catalysis
Abstract
The application of an alkyne cyclotrimerization regime with an [Fe(salen)]2 -μ-oxo (1) catalyst to triphenylmethylphosphaalkyne (2) yields gram-scale quantities of 2,4,6-tris(triphenylmethyl)-Dewar-1,3,5-triphosphabenzene (3). Bulky lithium salt LiHMDS facilitates a rearrangement of 3 to the 1,3,5-triphosphabenzene valence isomer (3'), which subsequently undergoes an intriguing phosphorus migration reaction to form the ring-contracted species (3''). Density functional theory calculations provide a plausible mechanism for this rearrangement. Given the stability of 3, a diverse array of unprecedented transformations was investigated. We report novel crystallographically characterized products of successful nucleophilic/electrophilic addition and protonation/oxidation reactions.
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Total citations:
6
Citations from 2024:
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(66.66%)
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Barrett A. N. et al. An Iron‐Catalyzed Route to Dewar 1,3,5‐Triphosphabenzene and Subsequent Reactivity // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 37.
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Barrett A. N., Diefenbach M., Mahon M. F., Krewald V., Webster R. L. An Iron‐Catalyzed Route to Dewar 1,3,5‐Triphosphabenzene and Subsequent Reactivity // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 37.
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TY - JOUR
DO - 10.1002/anie.202208663
UR - https://doi.org/10.1002/anie.202208663
TI - An Iron‐Catalyzed Route to Dewar 1,3,5‐Triphosphabenzene and Subsequent Reactivity
T2 - Angewandte Chemie - International Edition
AU - Barrett, A N
AU - Diefenbach, Martin
AU - Mahon, Mary F.
AU - Krewald, Vera
AU - Webster, R L
PY - 2022
DA - 2022/08/09
PB - Wiley
IS - 37
VL - 61
PMID - 35851715
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2022_Barrett,
author = {A N Barrett and Martin Diefenbach and Mary F. Mahon and Vera Krewald and R L Webster},
title = {An Iron‐Catalyzed Route to Dewar 1,3,5‐Triphosphabenzene and Subsequent Reactivity},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {61},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/anie.202208663},
number = {37},
doi = {10.1002/anie.202208663}
}