Decomposition of cyclic and linear N-acetyl-N-trimethylsilyl-amidophosphites

Пудовик, М. А.; Kibardina, L. K.; Medvedeva, M. D.; Anoshina, N. P.; Pestova, T. A.; Pudovik, A. N.

doi:10.1007/bf01179480

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1992

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“…The diphenyl "cinnamyl" phosphonate obtained appeared to be a mixture of isomers, resulting from a combination of Sn2 attack by phosphorus at the ( 1) position in cinnamyl chloride and Sn2' displacement at the ( 3 ) position. This is common with displacements on allylic systems, and has been previously observed with Arbuzov reactions (5).…”

Section: Discussionsupporting

confidence: 76%

Mixed metal vinyl stabilizer synergism. III: Reactions of mixed metals and phosphites with a model compound

Grossman

1992

J. Vinyl Addit. Technol.

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In the absence of mixed metal carboxylates, triaryl phosphites react rapidly with a model allylic compound for degrading vinyl, cinnamyl chloride, to yield phosphonium salts. On heating, these appear to yield allylidene phosphoranes by 1.1 elimination of HC1, with subsequent rearrangement to diphenyl phosphonates. With aryl alkyl phosphites, the phosphonium chloride intermediate undergoes rapid Arbusov rearrangement to the diphenyl phosphonate, eliminating alkyl chloride (or corresponding olefin). In the presence of zinc or cadmium carboxylates, Arbusov rearrangement is intercepted and chloride is transferred instead to the metal, forming the alkyl ester. The observed reaction paths appear to yield insight into the question of which phosphites are optimum for particular metal carboxylate blends and ratios in vinyl stabilizers, and into the related topic of which types of other additives are inappropriate.

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Section: Discussionsupporting

confidence: 76%

Mixed metal vinyl stabilizer synergism. III: Reactions of mixed metals and phosphites with a model compound

Grossman

1992

J. Vinyl Addit. Technol.

View full text Add to dashboard Cite

show abstract

Decomposition of cyclic and linear N-acetyl-N-trimethylsilyl-amidophosphites

Cited by 1 publication

References 0 publications

Mixed metal vinyl stabilizer synergism. III: Reactions of mixed metals and phosphites with a model compound

Mixed metal vinyl stabilizer synergism. III: Reactions of mixed metals and phosphites with a model compound

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