Synthesis and Stereoisomerization of Intra- and Intermolecularly Bridged Indigo
- 1 February 1984
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 57 (2) , 470-472
- https://doi.org/10.1246/bcsj.57.470
Abstract
The intramolecularly bridged N,N′-azelaoylindigo (3) and N,N′-sebacoylindigo (4) have been synthesized from indigo and the corresponding dichloride. The intermolecularly bridged N′,N″-sebacoylbis(N-acetylindigo) (5) has been synthesized from N-acetylindigo and sebacoyl dichloride. The relative rates of the cis-to-trans thermal isomerization of 3, 4, and 5, compared with that of N,N′-diacetylindigo (1c), were as follows: 3, 0.77; 4, 3.9; 5, 1.4; 1c, 1.0.This publication has 11 references indexed in Scilit:
- The Selective Preparation of N-AcylindigoBulletin of the Chemical Society of Japan, 1981
- Pigmente aus rötlichen Haaren und FedernAngewandte Chemie, 1974
- Excited state chemistry of indigoid dyes. II. Interaction of thio- and selenoindigo dyes with hydroxylic compounds and its implications on the photostability of indigoThe Journal of Physical Chemistry, 1973
- The isolation and structure of trichosiderin BCellular and Molecular Life Sciences, 1971
- cis-trans Isomerization and Pulsed Laser Studies of Substituted Indigo DyesJournal of the American Chemical Society, 1968
- Spectroscopic Studies on Dyes. V. Derivatives of cis-Indigo1The Journal of Organic Chemistry, 1965
- Spectroscopic Studies on Dyes. IV. The Fluorescence Spectra of Thioindigo Dyes1Journal of the American Chemical Society, 1957
- Spectroscopic Studies on Dyes. II. The Structure of N,N'-Dimethylindigo1Journal of the American Chemical Society, 1956
- The Relation between the Absorption Spectra and the Chemical Constitution of Dyes. XXVII. cis-trans Isomerism and Hydrogen Bonding in Indigo Dyes1Journal of the American Chemical Society, 1954
- The Relation between the Absorption Spectra and the Chemical Constitution of Dyes XXII. cis-trans Isomerism in Thioindigo Dyes1Journal of the American Chemical Society, 1951