Competition between Diels-Alder cycloaddition and spontaneous copolymerization of 1-methoxy-1,3-butadiene with electrophilic olefins

Autor:	H. K. Hall, Michael G. Mikhael, Anne Buyle Padias
Rok vydání:	1993
Předmět:	Olefin fiber Reaction mechanism Polymers and Plastics Organic Chemistry 1 3-Butadiene Maleic anhydride Cycloaddition Inorganic Chemistry chemistry.chemical_compound chemistry Electrophile Polymer chemistry Materials Chemistry Copolymer Reactivity (chemistry)
Zdroj:	Macromolecules. 26:4100-4104
ISSN:	1520-5835 0024-9297
DOI:	10.1021/ma00068a005
Popis:	Reaction of fumaronitrile with 1-methoxy-1,3-butadiene (MBD) at 25°C produced high molecular weight alternating copolymers and Diels Alder cycloadduct mixtures, even in dilute solutions. MBD reacted with maleic anhydride in bulk to produce mixtures of cycloadducts and low molecular weight alternating copolymers, while in solution only [4+2] cycloadducts were obtained. When the more electrophilic trisubstituted olefins trimethyl ethylenetricarboxylate, dimethyl cyanofumarate, and methyl β,β-dicyanoacrylate reacted with MBD, copolymerization competed with the concerted cycloaddition. Increasing electrophilicity of the olefin increased the yield of cycloadduct at the expense of that of copolymers
Databáze:	OpenAIRE
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