Reactions of 14‐hydroxy‐14‐azadispiro[5.1.5.2]pentadec‐9‐ene‐7,15‐dione and related compounds. II

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Abstract
3 When 11‐diethyl‐ and 3, 11‐di‐n‐propyl‐14‐hydroxy‐14‐azadispiro[5.1. 5.2]pentadec‐9‐ene‐7, 15‐dione (E‐IV and n‐Pr‐IV) are heated with polyphosphoric acid at 55–65°, the 14‐hydroxyl group cyclizes at the 11‐carbon to form E‐VI and n‐Pr‐VI, the structures of which have been established. Compounds P‐IV, i‐Pr‐IV and t‐B‐IV do not cyclize under these conditions.The Beckmann rearrangement of 12‐hydroxy‐12‐azadispiro[4.1.4.2]tridec‐8‐ene‐6, 13‐dione‐6‐oxime (P‐I) with polyphosphoric acid at 40–50° formed only the normal product, P‐II, which could not be cyclized.Compound P‐IV was the only ketone of this series which would add hydrogen cyanide to form a cyanohydrin.