1H‐1,3‐Benzazaphosphole (R = H, CH3, C6H5, N(CH3)2) bilden sich nicht nur aus o‐Aminophenylphosphin und verschiedenen Cyclisierungskomponenten wie RC(OR)NH· HCl, RC(O)Cl, HC(OR)3, RC(OCH3)2NR′2 oder Cl2CN(CH3)2Cl sondern auch aus sekundären o‐Aminophenylphosphinen PRHC6H4NH2 (R = C6H5, C2H5) und CH3C(OR)NH · HCl unter Abspalten von Ether sowie aus 1,3‐Benzazaphospholinen nach Oxydation oder thermischer Beanspruchung. Während sich 1,3‐Benzazaphosphole gegenüber Acetylchlorid oder Methyliodid indifferent verhalten, lassen sich aber die N‐Acetyl‐ und P‐Methyl‐1,3‐benzazaphosphole über das ambidente Anion gewinnen. Weitere Reaktionen der 1,3‐Benzazaphosphole und die NMR‐Daten der dargestellten Verbindungen werden diskutiert.

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mm.), 7 g. (40% based on acid used), Y = 1775 em.-'. A melting point of 56" has been reported17 for this lactone.4-(pToly1)pentanoic Acid.-The previous lactone was reduced according to the procedure of Martin.'* After 22 hr. the toluene layer was separated and extracted with dilute sodium hydroxide. The basic layer was acidified with hydrochloric acid and extracted with ether. The ether extracts were dried and the product distilled, b.p. 115" (1.5 mm.), 2.7 g. (38%). Boiling points of 173" (9 mm.)17 and 180' (14 mm.)8 have been reported. 4-(p-Tolyl)-l-pentanol.-The above acid was esterified with ethanol and hydrochloric acid. The ester, b.p. 144 (9 mm.),6,17 (17) H. Rupe and A. Steinback, Bsr., 44, 584 (1911). (18) E. L. Martin, J . A m . Chem. SOC. 68, 1438 (1936).was obtained as a colorless oil in 78% yield. A solution containing 2.3 g. of the ester in ether was added dropwise to a solution containing 0.47 g. of lithium aluminum hydride and the solution stirred at room temperature for 15 min. Excess hydride was destroyed with moist ether. The product was distilled in vacuo, b.p. 72-74' (0.1 mm.), 1.28 g. (62%). Simonsen' reports a boiling point of 151" (16 mm.) for this alcohol. Its infrared spectrum was identical with that of 11-2 and its 3,5-dinitrobenzoate melts a t 78" (reported6 m.p. 80').Infrared Spectra.-Infrared spectra were carried out unless otherwise specified on neat liquids using a Perkin-Elmer Model 21 spectrometer.Gas Chromatography.-A Model 154C Perkin-Elmer vapor fractometer was used with helium as the carrier gas under the conditions indicated in each case.The meso and racemic forms of 2,4-pentanediol have been separated from their mixture via fractional distillation of their cyclic sulfite esters, and their structures identified through their proton resonance spectra. The separated diols have been converted to diacetates, bis-3,5-dinitrobenzoates, dichlorides, and dibromides of corresponding structural symmetry and the isomeric pairs characterized. The reduction of acetylacetone by sodiumethanol, nickel-hydrogen, and sodium borohydride yielded the meso and racemic 2,4-pentanediols in the ratios 9:111 11:9, and 2:1, respectively.

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