Perfluoro-2,3-dimethylpenta-1,3-diene has been reacted with cold methanol to afford a monosubstituted product, whereas reaction in methanol containing triethylamine, even at ice temperature, formed a single multisubstituted product containing seven methoxy groups; these products have been fully characterised and their formation rationalised. Reactions of the diene with aniline and substituted anilines formed either pyrroloquinolines, azetines or oxoazetines. A rationalisation of the different reaction pathways in terms of the substitution pattern and electron demand of the substituents in the anilines is presented.
2001 substitution reactions substitution reactions O 0040
-036Reaction of Tetrafluoroethene Oligomers. Part 17. Some Reactions of (E/Z)-Perfluoro-2,3-dimethylpenta-1,3-diene.-Perfluoro-1,3-diene (I) reveals extremely high reactivity towards nucleophiles and considerably different results are obtained by small structural changes both in the substrate and in the nucleophile. In the reaction of (I) with cold methanol, four monosubstituted products are obtained, whereas reaction of (I) with methanol in the presence of triethylamine yields the multisubstituted product (VII). Reaction of diene (I) with anilines furnishes either pyrroloquinolines, e.g. (XII) and (XIII), oxoazetines (XV) or azetine (XVII). A rationalization of the reaction mechanism in terms of the substitution pattern and electron demand of the substituents in the anilines is given. -(BURNS, GRAHAM D.; COE, PAUL L.; ANDREWS, COLAN L.; Perkin 1 (2001) 5, 552-557; Sch. Chem., Univ. Birmingham, Edgbaston, Birmingham B15 2TT, UK; EN)
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