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- W2044845631 abstract "Abstract 2-Methyl-2H-cyclopenta[d]pyridazine reacts with trifluoracetic anhydride to give the 5- and 7-trifluoroacetyl products in about a 1:3 ratio. A series of HMO calculations have been made for similar ten π-electron heterocycles in an attempt to predict the positions in the 5-membered rings which would be most reactive to electrophilic substitution. The predictions based on the relative π-electron stabilities of the possible cationic intermediates are in accord with the available experimental data. If the atoms in the 6-ring are numbered 1-6 with the π-excessive heteroatom at the 1-position, then the most reactive site to electrophilic substitution in the 5-ring will be the atom which is linked to either the 1-, 3- or 5-positions. The structures of the major and minor trifluoroacetyl isomers of 2-methyl-2H-cyclopenta[d]pyridazine have been determined by X-ray crystallographic analyses, and the HMO predictions agree with the finding that C(7) is the most reactive position. 2-Methyl-5-trifluoroacetyl-2H-cyclopenta[d]pyridazine crystallizes in the monoclinic space group P21/m, cell constants a = 8·109, b = 6·713, c = 8·768 A, β = 91·88°, with two molecules per unit cell. All of the atoms have been located and refined by full-matrix least-squares and the final residual is 0·056. The bond lengths appear to be influenced by a contribution of a pyridazinium form to the resonance hybrid. 2-Methyl-5-bromo-7-trifluoroacetyl-2H-cyclopenta[d]pyridazine crystallizes in the orthorhombic space group Pnam, cell constants a = 12·920, b = 12·513, c = 6·752 A, with four molecules per unit cell. Although the quality of the diffraction data was severely limited by rapid decomposition of the specimen in the X-ray beam, the gross features of the structure were revealed. The residual following isotropic refinement was 0·19." @default.
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- W2044845631 date "1970-01-01" @default.
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- W2044845631 title "The position of electrophilic substitution of 2-methyl-2H-cyclopenta[d]pyridazine and the crystal structures of two substitution products" @default.
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- W2044845631 doi "https://doi.org/10.1016/0040-4020(70)80007-2" @default.
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