The i.r. spectra of the p forms of phthalocyanine and its A"'-dideuterio-derivative are recorded. Absorptions resulting from N-H vibrations are assigned to bands a t 3273, 1539, and 735 cm-l. Other differences between the spectra of the parent and the dideuterio-derivative in the 760-71 0 c m -l region are explained in terms of a lattice vibration, modified by a second-order isotope effect. SINCE Cannon and Sutherland first recorded the i.r. spectrum of phthalocyanine (l), there has been much discussion concerning the assignment of absorption bands to the N-H vibrational modes of the molecule.At least three conflicting reports 2-4 appeared and other authors 6*6 have joined the discussion.Frigerio2 recorded that the i.r. spectrum of the a polymorph of (1) and its NN'-dideuterio-derivative (2) are identical in the range 4000-850 cm-l, and concluded that the weak absorption observed at 3298 cm-l does not arise from an N-H stretching mode.Sidorov and Kotlyar3 prepared both the a and p forms of (1) and (2) and observed a number of differences in the spectra attributable to isotopic effects. Although their deuteriated samples were contaminated with (1) and monodeuterio-derivative, they were able to make assignments to N-H and N-D vibrational modes.

Treatment of N-(2,6-dimethyl-4-oxopyridin-l -yl) -pyridinium, -quinolinium, and -isoquinolinium salts with trialkyl phosphites in the presence of sodium iodide gives regiospecifically dihydro-intermediates, which may be decomposed in good yields to dialkyl pyridin-4-yl-, quinolin-4-yl-, and isoquinolin-1 -yl-phosphonates respectively. The reaction may also be carried out in one step without isolating the dihydro-intermediate.

N-(2,6-Dimethyl-4-oxopyridin-1 -yl)pyridinium salts (4), new reagents for the regiospecific synthesis of 4substituted pyridines, give moderate to high yields of 4-alkyl-and 4-aryl-pyridines (8)-(10) on reaction with Grignard reagents. The scope and limitations of the reaction, which proceeds via 1,4-dihydro-intermediates (5)-(7), are explored. No 2-substituted pyridines were detected. Some reactions with organolithium compounds are also described.

reported herein gave spectral data in full accord with the assigned structures. New compounds which were sufficiently stable to allow for full characterization gave satisfactory elemental analyses and/or molecular weight measurements (high resolution mass spectrometry). 17) G. H. Posner, D. J. Brunelle, L. Sinoway, Synthesis 1974, 662. (81 In the case of [(6a)-(6d)], silyl enol ether formation was highly regioselective [exclusive or nearly exclusive formation of (70)-(7d)].-When lithium 2.2.6.6-tetramethylpiperidide was used as a base in the place of lithium diisopropylamide, (10) was formed as the major product.191 For studies related to the thermal rearrangement of methylene(viny1)cyclopropane systems, see also W E.

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