STRUCTURES AND PHOTOCHROMIC PROPERTIES OF SUBSTITUTED SPIROINDOLINONAPHTHOXAZINES

Citation
Sm. Aldoshin et al., STRUCTURES AND PHOTOCHROMIC PROPERTIES OF SUBSTITUTED SPIROINDOLINONAPHTHOXAZINES, Russian chemical bulletin, 47(6), 1998, pp. 1089-1097
Citations number
19
Categorie Soggetti
Chemistry
Journal title
ISSN journal
10665285
Volume
47
Issue
6
Year of publication
1998
Pages
1089 - 1097
Database
ISI
SICI code
1066-5285(1998)47:6<1089:SAPPOS>2.0.ZU;2-H
Abstract
Six indolinospironaphthoxazines were studied by X-ray diffraction anal ysis. demonstrated that the electronic nature of the substituents in t he naphthoxazine and indoline fragments has no substantial effect on t he C-spiro-O and C-spiro-N bond lengths. Photocolorability of the comp ounds under study depends only slightly on the above-mentioned bond le ngths and correlates mainly with the energy of steric strain of the ox azine ring. The stability of the open forms of spiroindolinonaphthoxaz ines that formed upon photoirradiation is determined to a large extent by the electronic and steric nature of the substituents. The exceptio n is the compound that contains the NO2 group in the indoline fragment . In the last-mentioned case, the cleavage of the ring occurs through a substantially different pathway.