The Reaction of Phosphite Esters and Tris(dimethylamin0)phosphine With 1,4- Naphthoquinonemonobenzenesulfonimine

Zayed, M. F.; El-Khoshnieh, Yehia O.; El-din, N. Khir; Boulos, L. S.

doi:10.1080/10426509008042123

Cited by 4 publications

(2 citation statements)

References 18 publications

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“…Reaction with P(NMe 2 ) 3 instead of phosphite furnished directly the stable zwitterionic 1,6addition product 109 (Scheme 31c). [217] Studies with the PH-functional dialkyl phosphites proved that the addition to p-benzoquinone depends on the reaction conditions. In the presence of alkali metal alkoxides [218] or Et 3 N [219,220] only 1,6-addition to 107 OAlk is observed.…”

Section: O-hydroxy-and Related + M-substituted Aryl-phosphanes -Phosp...mentioning

confidence: 99%

“…For the reaction of trimethyl‐ and triisopropyl phosphite with 1,4‐naphthoquinone‐benzenesulfonimine in benzene the 1,4‐addition products with Et + ‐translocation to the N‐atom ( 110) were precipitated, the methyl compound in low yield (25 %), the i Pr‐derivative after addition of petroleum ether in 95 % yield. Reaction with P(NMe 2 ) 3 instead of phosphite furnished directly the stable zwitterionic 1,6‐addition product 109 (Scheme 31c) [217] …”

Section: Routes To 2‐hydroxyarylphosphanesmentioning

confidence: 99%

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o‐Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable Ambiphiles with Multiple Applications

Heinicke

2023

Chemistry A European J

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o‐Hydroxyarylphosphanes are fascinating compounds by their multiple‐reactivity features, attributed to the ambident hard and soft Lewis‐ and also Brønstedt acid‐base properties, wide tuning opportunities via backbone substituents with ±mesomeric and inductive, at P and in o‐position to P and O also steric effects, and in addition, the configurational stability at three‐valent phosphorus. Air sensitivity may be overcome by reversible protection with BH3, but the easy oxidation to P(V)‐compounds may also be used. Since the first reports on the title compounds ca. 50 years ago the multiple reactivity has led to versatile applications. This includes various P‐E‐O and P=C‐O heterocycles, a multitude of O‐substituted derivatives including acyl derivatives for traceless Staudinger couplings of biomolecules with labels or functional substituents, phosphane‐phosphite ligands, which like the o‐phosphanylphenols itself form a range of transition metal complexes and catalysts. Also main group metal complexes and (bi)arylphosphonium‐organocatalysts are derived. Within this review the various strategies for the access of the starting materials are illuminated, including few hints to selected applications.

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Section: O-hydroxy-and Related + M-substituted Aryl-phosphanes -Phosp...mentioning

confidence: 99%

Section: Routes To 2‐hydroxyarylphosphanesmentioning

confidence: 99%

o‐Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable Ambiphiles with Multiple Applications

Heinicke

2023

Chemistry A European J

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ChemInform Abstract: The Reaction of Phosphite Esters and Tris(dimethylamino)phosphine with 1,4‐Naphthoquinonemonobenzenesulfonimine.

et al. 1990

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Reactions of p‐quinone monoimines with lawesson reagent and phosphorus pentasulfide

Boulos¹,

Hennawy²,

Arsanious³

1994

Heteroatom Chemistry

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The Reaction of Phosphite Esters and Tris(dimethylamin0)phosphine With 1,4- Naphthoquinonemonobenzenesulfonimine

Cited by 4 publications

References 18 publications

o‐Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable Ambiphiles with Multiple Applications

o‐Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable Ambiphiles with Multiple Applications

ChemInform Abstract: The Reaction of Phosphite Esters and Tris(dimethylamino)phosphine with 1,4‐Naphthoquinonemonobenzenesulfonimine.

Reactions of p‐quinone monoimines with lawesson reagent and phosphorus pentasulfide

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