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EnglishThe gas-phase methylation of furan (I) or thiophene (II) by radiolytically generated Me2X+ (X = F, Cl) is examd. by their competitive reaction with C6H6. The mechanism of the substitution, and of the subsequent isomerization, occurring via intramol. 1,2 Me-group shifts, is related to the reactions regiochem. As for pyrroles, gas-phase Me2F+ methylation of I and II is characterized by a scarce substrate discrimination (relative to C6H6), accompanied by an appreciable positional selectivity toward those substrate positions with the highest neg. net charge. On the contrary, Me2Cl+ confirms its inherent affinity toward n-type nucleophilic centers by attacking preferentially the heteroatom of I and II. Gas-phase attack of Me2X+ on simple 5-membered heteroaroms. is essentially regulated by the electrostatic interaction established within the encounter pair. A close correspondence does exist between this rationalization of the present gas-phase results and recent theor. predictions.
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| Titolo: | Gas-phase heteroaromatic substitution. 3. Electrophilic methylation of furan and thiophene by MeXMe+ (X = fluoro, chloro) ions | |
| Autori: | ||
| Data di pubblicazione: | 1982 | |
| Rivista: | ||
| Handle: | http://hdl.handle.net/11573/460188 | |
| Appartiene alla tipologia: | 01a Articolo in rivista |
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