Naslov
Ferrocene Compounds. XXVI. C- and O-Ferrocenylalkylation of Methyl Salicylate

Autori
Kovač, Veronika ; Rapić, Vladimir ; Alagić, Jasmina ; Barišić, Lidija

Izvornik
Croatica chemica acta (0011-1643) 72 (1999), 1; 103-113

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
ferrocene; o-ferrocenylalkylation; methyl salicylate; 1-ferrocenylethyl ether; methyl 3/5-ferrocylsalicylates; methyl 5(2-ferrocenylethyl)salicylate; alpha- and beta-ferrocenyl carbocations

Sažetak
Reaction of equimolar amounts of methyl salicylate, sodium and N,N,N-trimethylferrocylammonium iodide (1a) in ethanol gave 55% of ethyl 1-ferrocenylethyl ether (4). By refluxing a solution of 9 mmol sodium and 3 mmol of FcCHRNMe3I (1a, R=H; 1b, R=Me; 1c, R=Ph) in a large excess of methyl salicylate for 2-3 hours, the corresponding methyl 5-ferrocylsalicylates (5) (10-23%) and methyl-3-ferrocylsalicylates (6) (12-20%) were obtained. During conversion of salt 1b, besides of 5b and 6b, 20% of vinylferrocene (7) and 6% of 1-ferrocenylethyl ether (8) were isolated. Under the same conditions as in conversions 1_5,6 2-ferrocenylethyl acetate (11) and methyl salicylate failed to react, and 2-ferrocenylethyl bromide (12) was transformed to 12% of methyl o-(2-ferrocenylethoxy)benzoate (13) and 25% of methyl 5-(2-ferrocenylethyl)salicylate (14), as well as 10% of vinylferrocene (7). The mechanisms of reactions 1_5,6 and 12_13,14 are discussed, suggesting a stabilization effect by ferrocene nucleus in the intermediate alpha- and ß-ferrocenyl carbocations.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA