Novel chain transfer agents
a technology of chain transfer agent and chain transfer agent, which is applied in the field of new chain transfer agent class, can solve the problems of inability to design agents to impart useful chemical functionality at both ends of the polymer chain, high cost of higher molecular weight agents, and inability to meet the requirements of high-temperature processing, etc., and achieves the effect of convenient and economical synthesizing and versatile in their applications
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example 1
Synthesis of 1-Phenylvinyl Diphenylphosphinate
[0109] Methyl diphenylphosphinite (67.5 g, 0.312 mol) was added to hexane (200 mL) in a 500 ml round bottom flask under inert atmosphere (constant flow of dry argon). The solution was then cooled to -78.degree. C. by immersion of the reaction vessel into a dry ice / acetone bath. The methyl diphenylphosphinite was observed to freeze out of solution. To the reaction vessel at reduced temperature, chloroacetophenone (48.3 g, 0.313 mol) in chloroform (140 ml) was added. The reaction vessel was allowed to warm to room temperature over three hours with constant stirring and argon flow. As the methyl diphenylphosphinite melted into the solution, a white precipitate formed. After completion of the three hour reaction time, the crude product was obtained by removal of hexane and chloroform. H-NMR analysis of the crude product showed 86.7% of the desired Perkow product, 13.3% Arbusov byproduct, and no methyl diphenylphosphinite starting material. T...
example 2
Synthesis of 1-Methylvinyl Diphenylphosinate
[0111] Methyl diphenylphosphinite (4.92 g, 22.7 mmol) was dissolved in chloroform (2 ml) in a 15 ml round bottom flask under inert atmosphere (constant flow of dry argon). The solution was then cooled to -78.degree. C. by immersion of the reaction vessel into a dry ice / acetone bath. The methyl diphenylphosphinite was observed to freeze out of solution. To the reaction vessel at reduced temperature, a solution of chloroacetone (1.8 ml, 22.5 mmol) in chloroform (1 ml) was added. The reaction vessel was allowed to warm to room temperature over three hours with constant stirring and argon flow. As the methyl diphenylphosphinite melted into the solution, the reaction proceeded. After the completion of the three hour reaction time, the crude product was obtained by removal of the chloroform. Recrystallization from hot hexane followed by drying for 12 hours in a vacuum oven (60.degree. C. 6 mm Hg) yielded 1-methylvinyl diphenylphosphinate (4.62 g...
example 3
Synthesis of 1-Phenylvinyl Methyl Phenylphosphonate (1-PVMPP)
[0112] Under a constant flow of dry nitrogen, 2-chloroacetophenone (17.3 g, 112 mmol) was melted in a 100 ml round bottom flask using a 65.degree. C. oil bath. The flask was equipped with a magnetic stir bar and an addition funnel with a pressure-equalizing sidearm. Dimethyl phenylphosphonite (23.0 g, 135 mmol) was then added dropwise (21.5 ml via addition funnel) to the melted chloroacetophenoneover the course of 1.25 hour. The evolution of a gas, presumably methyl chloride, was observed throughout the course of the addition and was perceived as evidence for formation of product.
[0113] After the 1.25 hour, 26.7 g (97 mmol, 86.4%) of the pale yellow liquid product 1-PVMPP was obtained by vacuum distillation (175.degree. C. 2 mm Hg). The proton NMR spectrum of the product in CDCl.sub.3 shows the expected resonances (relative to TMS at 0.0 ppm) at 3.4-3.8 ppm correlating to the 3 methoxy protons, 4.8-5.1 ppm for the 2 vinyl ...
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