Abstract
C~sH,3N; M r = 207.3; monoclinic, space group P2/c; a = 19.972 (5), b = 5.537 (1), c = 21.530 (4) A, fl = 110.22 (2)°; D c = 1.232 gcm -3 for Z = 8. Mo Ka radiation diffractometer data. Final R = 0-055. C-C bond lengths show the influence of considerable single-double bond alternation. Crystal- packing interactions in the ac plane are limited to H...H contacts, whereas C...C contacts are the primary interactions in the b direction. Introduction. The title compound (II) was prepared as follows: 2-methyl-3-chloroisoquinolinium iodide (I) (13-5 g, 0.45 mol) was added to freshly prepared sodium cyclopentadienide (from 5.6 g, 0.24 mol, sodium sand and 33 ml, 0.43 mol, cyclopentadiene) in 250 ml dry dimethoxymethane under nitrogen with stirring. After 16 h at room temperature, the reaction was quenched with water, the aqueous solution was extracted with benzene, and alumina thin-layer chromatography (benzene eluent) of the concentrated benzene fraction revealed three mobile components (one major purple band, two minor yellow-green bands) in addition to a brown-black band at the origin. The purple component was isolated by column chromatog- raphy (neutral alumina, benzene eluent), and following sublimation and recrystallization from benzene, there was obtained a 2% yield of (II) as purple needles, m.p. 105-106.5 °C.
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