2007
DOI: 10.1016/j.jorganchem.2007.05.020
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Products of hydrolysis of (ferrocenylmethyl)trimethylammonium iodide: Synthesis of hydroxymethylferrocene and bis(ferrocenylmethyl) ether

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Cited by 22 publications
(15 citation statements)
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“…Another less polar ferrocenyl compound was also present but could not be identified. Interestingly, we recently found that 5 was a side-product of the coupling of (ferrocenylmethyl)trimethylammonium iodide and 1,4,7-(triformyl)-1,4,7,10-tetraazacyclododecane to give 1-(ferrocenemethyl)-4,7,10-(triformyl)-1,4,7, 10-tetraazacyclododecane in aqueous solution [27]. A possible pathway for the formation of 3-5 is presented in Scheme 1 and involves the simultaneous formation of 3 and the carbocation 6 which has been previously reported to be stabilised in acidic media [28][29][30][31].…”
Section: Resultsmentioning
confidence: 99%
“…Another less polar ferrocenyl compound was also present but could not be identified. Interestingly, we recently found that 5 was a side-product of the coupling of (ferrocenylmethyl)trimethylammonium iodide and 1,4,7-(triformyl)-1,4,7,10-tetraazacyclododecane to give 1-(ferrocenemethyl)-4,7,10-(triformyl)-1,4,7, 10-tetraazacyclododecane in aqueous solution [27]. A possible pathway for the formation of 3-5 is presented in Scheme 1 and involves the simultaneous formation of 3 and the carbocation 6 which has been previously reported to be stabilised in acidic media [28][29][30][31].…”
Section: Resultsmentioning
confidence: 99%
“…The Fe-C and FeÁ Á ÁCg distances to the substituted 5 -C 5 H 4 X ring are slightly shorter than those for the 5 -C 5 H 5 ring, which is attributed to the substituent in the 5 -C 5 H 4 X ring. The shortening of these distances in (I)-(III) is statistically not significant but this trend was observed for all other monosubstituted ferrocenes, whether the substituent is an electron-donating or an electron-withdrawing group (Kaluski & Struchkov, 1966;Sato, Iwai et al, 1984;Sato, Katada et al, 1984;Drouin et al, 1997;Foucher et al, 1999;Lin et al, 1998;Alley & Henderson, 2001;Hnetinka et al, 2004;Nemykin et al, 2007;Gasser et al, 2007).…”
Section: Commentmentioning
confidence: 82%
“…In 12 , the torsion angle made by the C(9)–C(11) bond with the fivefold axis of the ferrocenyl unit is 101° (175° in 11 ). For comparison, the parent ether, [(C 5 H 5 )Fe(C 5 H 4 ‐CH 2 )] 2 O, also adopts C 2 symmetry such that the dihedral angle C(9)–C(11)–C(11*)–C(9*) is now 131.8°, but the angle at the central oxygen (112.8°) is smaller than in the dianthracenyl analogue 12 .…”
Section: Resultsmentioning
confidence: 99%