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Additional resources for Chemistry of Heterocyclic Compounds: The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth, Volume 1

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1 g of dichloride) and the acid, isolated by evaporation of the final solution, was identified solely by a phosphorus analysis, its identity must remain uncertain. The phosphetane ring occurs in other compounds in which it is fused to other ring systems (cf, p. 154). Five-Membered Ring Systems containing only Carbon and One Phosphorus Atom Phospholes, Phospholenes, and Phospholanes Phosphole has the formula (l),[RRI 148, in which the molecule is depicted inverted, with the phosphorus atom a t the top]; it can be regarded as the phosphorus analogue of pyrrole, but i t has many markedly different properties.

P. p. p. 3 mm. McCormack's reaction was of great value in providing ready access t o phospholenes, but this value was initially limited by the fact that the final hydrolyzed products were the highly stable phospholene 1-oxides. , the oxygen was removed without hydrogenation of the phospholene ring. Balon claims that these substituted 3-phospholencs and also substituted phospholanes (p. 61) are of value for catalyzing the conversion of isocyanates into carbodiimides : 2CeHrNCO -+ CaH5N=C=NCsH5 + CO2 After testing various members in each series, he decided that 3-methyl1-phenyl-3-phospholene and 1-ethyl-3-methylphospholanewere the most effective members in their respective series for this purpose.

A number of 1-substituted 3-phospholenes were thus isolated, and they were characterized by quaternization with benzyl bromide to give the crystalline 1 -substituted 1-benzyl-3-phospholenium bromides (Quin and Mathewes 50). Since the McCormack reaction was regarded as a particular type of Diels-Alder reaction, it was natural to assume that the product was a 3-phospholene, and they have been so depicted in the foregoing pages to avoid confusion. Fresh light was thrown on this subject some 10 years ~ , showed later by the work of Hasserodt, Hunger, and K ~ r t e ,5 7~ who that 1,3-dienes would also combine with phosphorus trichloride (with the usual addition of copper stearate), although at 20" the reaction was sometimes not complete after 60 days.

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