TWOFOLD RING-CLEAVAGE OF 2,3,5,6-TETRAHYD RO-10BH-OXAZOLO[2,3-A]ISOQUINOLINE WITH SALTS OF HYDROXYLAMINE DERIVATIVES

Contrary to literature the reaction of the cyclic carbinolamine ether 1 with hydroxylamine hydrochloride don't give the N-hydroxyaminal hydr ochloride 2 . HCl, but the ring opened E-oxime amine hydrochloride 3 . HCl. The structure is proved with NMR- and UV-spectroscopic methods. Similar products 11 . HCl - 15 . HCl and 18 . HCl/19 . HCl are availab le from salts of hydroxylamine ethers and semicarbazides. The reactivi ty of 1 and the stability of the products are investigated.