1-(2,4,6-Tri-tert-butylphenyl)-3-methylphosphole:  A Phosphole with a Significantly Flattened Phosphorus Pyramid Having Pronounced Characteristics of Aromaticity

Abstract

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Phospha‐Organic Chemistry: Panorama and Perspectives

“…At present, the most impressive increases in aromatic reactivity have been obtained with the very bulky 2,4,6-tris(tert-butylphenyl) substituent at the phosphorus center. [197] The corresponding phosphole 28 is almost planar: sum of the C-P-C angles 331.78. The out-ofplane angle of the PÀR bond is reduced from 66.9 in 1-benzylphosphole to 45.08, and the PÀC intracyclic bonds from 1.786 (mean) to 1.743 .…”

“…(71)]. [197] Dibromophosphination at a ring carbon atom is also possible by using phosphorus tribromide. [198] In the same vein, C-acylation can also be performed on phosphole-Mo(CO) 5 complexes.…”

New P‐ligands: The aromaticity and reactivity of 2,4,6‐trialkylphenylphospholes

“…The synthesis, properties, and reactivity of 2,4,6-trialkylphenylphospholes were described in earlier publications [1][2][3][7][8][9][10][11][12]. In this paper, the recent findings of ours on the physical and chemical properties of trialkylphenylphospholes are discussed.…”

“…For arylphospholes 1a and 1b, the sum of the angles at the phosphorus atom, introduced by Schmidpeter as the measure of flattening [14], was found to be 314.4 [2] and 331.7 [3], respectively. For phospholes with pyramidal geometry at P, this number is around 302 [15].…”

The synthesis of six‐membered P‐heterocycles with sterically demanding substituent on the phosphorus atom

“…A bulky P-substituent, such as the 2,4,6-trialkylphenyl group, may have an impact on the geometry around the P-pyramid [2][3][4]. On the other hand, the reactivity of the P O moiety is also influenced by the presence of the trialkyphenyl substituent [5,6].…”