SYNTHESIS AND NMR-STUDY OF 9'-SUBSTITUTED SPIROINDOLINONAPHTHOXAZINE DERIVATIVES

A photochromic spiroindolinonaphthoxazine derivative, 1,3,3-trimethyl-9'-hydroxy-spiro[indoline-2,3'(3H)-naphtho[2,1-b][1,4]oxazine] 3 was synthesized by condensation of 1,2,3,3-tetramethylindolenium iodide 1 and 1-nitroso-2,7-dihydroxynaphthalene 2. Further, two new derivatives, 5 and 7, were prepared in good yields by the reactions of 3 with the hexafluoropropene trimer 4 and 4-[perfluoro(2-isopropyl-1,3-dimethyl-1-butenyl)oxybenzoyl chloride 6, respectively. Their unique structural features and property are discussed based on H-1-, C-13- and F-19 nmr spectral data.