Coumarins XIV: high-resolution mass spectra of 3',4'-disubstituted 3',4'-dihydroseselins

High-resolution mass spectra of 14 3',4'-disubstituted 3',4'-dihydroseselins were examined. The nature of the substituents determinines the mode of fragmentation. Compounds having one or two acyloxy substituents fragment mainly by a pathway leading to the stable coumarinopyrilium ion. Coumarins with alkoxy or hydroxy substituents proceed by way of fission of the chroman ring, accompanied by the loss of two ring carbon atoms. Several generalizations are formulated which will aid in the interpretation of the mass spectra of this class of coumarins from a structural standpoint.