2006
DOI: 10.1134/s1070428006010155
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Degenerate rearrangement of detectable 9,10-dimethyl-9-vinyl-phenanthrenium ion: 1,2-Shift of the vinyl group

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Cited by 8 publications
(9 citation statements)
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“…Nitrosonium complex of 1,10 phe nanthroline (27) can serve as an example. 68 A rapid de generate rearrangement is also characteristic of this com plex ( Scheme 14).…”
Section: Scheme 13mentioning
confidence: 99%
“…Nitrosonium complex of 1,10 phe nanthroline (27) can serve as an example. 68 A rapid de generate rearrangement is also characteristic of this com plex ( Scheme 14).…”
Section: Scheme 13mentioning
confidence: 99%
“…Thus the calculations showed the lack of conformational control over 1,2-shift of cyclopropyl group, in contrast to 1,2-shift of vinyl group. Vinyl group migration from conformer like A is considerably more favorable than from conformer B [22]. Pair averaging of the chemical shifts of protons in the cyclopropyl group (H b /H e , H c /H d ) indicates that migration of the cyclopropyl group is not accompanied by change of its configuration (cf.…”
mentioning
confidence: 96%
“…The rate of 1,2-shift of cyclopropyl group is considerably higher than the rate of migration of methyl [10,19], ethyl [14], and phenyl groups [20,21,15] but is lower than the rate of 1,2-shift of vinyl group [22] (cf. [17]).…”
mentioning
confidence: 99%
“…When R = H [6], Et [2], ClCH 2 [7], Cl 2 CH [5], CH 2 =C(Me) [11], Ph, p-MeC 6 H 4 , p-FC 6 H 4 , m-FC 6 H 4 , p-F 3 CC 6 H 4 , C 6 F 5 [3], O 2 N [7], the equilibrium is displaced toward β-isomer, whereas α-and β-isomeric carbocations with R = p-MeOC 6 H 4 [3], CH 2 =CH [10], trans-MeCH=C(Me) [11], cyclopropyl [12], and Cl [4] are characterized by comparable stabilities. Therefore, for most of the above listed migrating groups we succeeded in determining by dynamic NMR the rate of 1,2-shift, not being concerned about almost complete transformation of β-isomer I into α-isomer as a result of 1,2-shift of methyl group.…”
mentioning
confidence: 99%
“…Long-lived 9-R-9,10-dimethylphenanthrenyl cations are capable of undergoing degenerate rearrangement via 1,2-shift of the R substituent (Scheme 1) and are therefore convenient models for studying relative migration abilities of various atoms and groups [2][3][4][5][6][7][8][9][10][11][12].…”
mentioning
confidence: 99%