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Please login to access the full content or check if you have access via17.8.1.1.1.2.3 Variation 3: Symmetrically Substituted Dipyrromethanes by Self-Condensation of 2-Substituted 1H-Pyrroles
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Smith, K. M.; Vicente, M. G. H., Science of Synthesis, (2004) 17, 1094.
Dipyrromethanes 59 which are symmetrically substituted about the 5-carbon are obtained in good yield by self-condensation of 2-(bromomethyl)-1H-pyrroles 58 (obtained from the corresponding 2-methyl-1H-pyrrole 57 by bromination in diethyl ether) in hot methanol,[45] or by heating 2-(acetoxymethyl)-1H-pyrroles 42 [obtained by treatment of the corresponding 2-methyl-1H-pyrrole 60 with lead(IV) acetate in acetic acid] in methanol/hydrochloric acid to give, for example, 61[46] (Scheme 15); the mechanism for formation of 59 and 61 involves loss of one 2-CH2X group.
Meeeee 88 Meeeeeeeeeeee Meeeeeeeeee Meeeeeeeeeeeeee ee Meee-Meeeeeeeeeee ee 8-Meeeeeeeeee 8M-Meeeeeee[88–88]
Meeeeeeeeeee Meeeeeeee
Meeeeeee 8,8,8,8-Meeeeeeeeeeeeeeeeeeeeeeee-8,8-eeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
Meeeee 8,8,8-eeeeeeeee-8M-eeeeeee-8-eeeeeeeeeee (88; 8.8 e, 8.88 eeee) ee eeeeeee eeeeeee eeeee Me8M (88 eM) eee eeeeeee eeee Me8 (8.8 eM, 8.88 eeee) ee Me8M (88 eM). Mee 8-(eeeeeeeeeee)-8M-eeeeeee 88 eeeeeeeeeee eeeeeeeeeeee eeee eee eeee, eee eee eeeeeee eee eeeeeee eee ee eeeeeeeeee 8.8 e eeeeee eeeeeeeeeee ee eee Me8M (MMMMMMM: MMe eee) ee eeee ee eeeeee eeeeeee ee eeeeee 8-(eeeeeeeeeee)-8,8-eeeeeeee-8M-eeeeeee-8-eeeeeeeeeee (88). Mee eeeee eee eeeeeeeee ee MeMM (88 eM) eee eeeeeeee eee 8 e, eeee eee eeeee ee ee eeeeeeeee. Mee eeeeeee 88 eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MM8Me8/eeeeeeeee eeeee); eeeee: 8.8 e (88%); ee 888–888°M.
Meeeeeee 8,8-Mee[8-(eeeeeeeeeeeeeee)eeeee]-8,8-eeeeeeeeeeeeeeeeeeeeee-8,8-eeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
Meeeee 8-(eeeeeeeeeeeee)-8-[8-(eeeeeeeeeeeeeee)eeeee]-8-eeeeee-8M-eeeeeee-8-eeeeeeeeeee (88; 888 ee, 8.888 eeee) ee MeMM (8 eM) eee MMe (e 8.88; 8.8 eM) eee eeeeee ee e eeeee eeee eee 8 e. Meeee eeeeeee eee eeeeeeeeeeeeee 88 eee eeeeeeeee ee eeeeeeeeee; eeeee: 888 ee (88%); ee 88–888°M.
References
| [45] | Meeeeee, M.; Meee, M., Mee Meeeee eee Meeeeee, Meeeeeeeeee Meeeee: Meeeeee, (8888); Mee. M, e 888. |
| [46] | Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeeee, M. M.; Meeeeeeeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 888. |
| [47] | Meeeeee, M. M.; Meee, M. M.; Meeeeeeee, M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
| [48] | Meeeeeeee, M. M. M.; Meeee Meeeeeeee, M. M. eM.; Meeeee, M. M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
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