The Preparation and Reactions of Diphenylphosphinous Chloride

Stuebe, Carl; LeSuer, William M.; Norman, Gilman R. Van

doi:10.1021/ja01618a030

Cited by 58 publications

(8 citation statements)

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“…,P-SR' + R"X -R"J " 7 /p-R" (20) Perhaps due to the lesser strength of the carbonsulfur bond as compared to the carbon-oxygen bond, the rearrangement of the sulfur analogues is more rapid than that of the phosphinites.217, 218 The intermediate phosphonium salts also can be isolated if the reaction is carried out at low temperature. 219 In a similar manner alkyl phosphonamidothionites Fluorinated ketones also react unusually with silyl and acetyl phosphites222 (eq 22, 23).…”

Section: Behavior Of Sulfur and Fluorine Analogues Under Arbuzov Cond...mentioning

confidence: 99%

Michaelis-Arbuzov rearrangement

Bhattacharya¹,

Thyagarajan²

1981

Chem. Rev.

810

413

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Contents I. Introduction 415 II. Reaction Mechanism 416 III. Scope and Limitation of the Reaction 417 A. Alkyl Halides 418 B. Tricoordinate Phosphorus Reactant 420 C. Effectiveness of Catalysts 421 IV. Synthetic Applications 421 A. Synthesis of Phosphonates 421 B. Synthesis of Phosphinates 422 C. Synthesis of Tertiary Phosphine Oxides 423 D. Synthesis of Phosphonyl and Phosphinyl Halides 424 E. Other Synthetic Applications 424 V. Behaviour of Sulfur and Fluorine Analogues under Arbuzov Conditions 425

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Section: Behavior Of Sulfur and Fluorine Analogues Under Arbuzov Cond...mentioning

confidence: 99%

Michaelis-Arbuzov rearrangement

Bhattacharya¹,

Thyagarajan²

1981

Chem. Rev.

810

413

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“…Diphenylphosphinous chloride was prepared by a previously described method. 28 Di(chlorophenyl)phosphinous chloride was also prepared by the above method; b.p. 144-150°/0.3-0.4 mm., n20D 1.5900.…”

Section: Experimental27mentioning

confidence: 99%

Acetylene-Allene Rearrangements. Reactions of Trivalent Phosphorus Chlorides with α-Acetylenic Alcohols and Glycols

Boisselle¹,

Meinhardt²

1962

J. Org. Chem.

119

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“…Selection of a suitable oxidizing agent can be troublesome, as readily oxidizable alkyl groups on the phosphorus atom and on the side chains of aromatic substituents may be involved in the reaction. The references to oxidation of phosphines with alkyl or aryl peroxides (29,40,51,55), hydrogen peroxide (44, 59, 71, 95,97,101), nitrogen tetroxide (1), nitric acid (91, 100), and amine oxides (57) denote work done in this area since 1950. It should be mentioned also that phosphines are frequently converted to the oxides upon standing in air or in the presence of oxygen (5,69).…”

Section: The Use Of Lithium Reagentsmentioning

confidence: 99%