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Polymerizable mesoionic 4,6‐dioxo‐1,3‐diazines, 1. Synthesis and photochemical behavior of polystyrenes with mesoionic 4,6‐dioxo‐1,3‐diazines as pendant groups
Author(s) -
Ritter Helmut,
Sperber Rolf,
Weisshuhn Carl Michael
Publication year - 1994
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1994.021951208
Subject(s) - mesoionic , diazine , chemistry , polystyrene , polymer chemistry , pyridazine , alkyl , isocyanate , organic chemistry , polymer , polyurethane
Mesoionic 5‐alkyl‐4,6‐dioxo‐1,3‐diphenyl‐2‐(3‐vinylbenzylthio)‐1,3‐diazine ( 6 ) was prepared by condensation of alkylmalonic acid ( 5 ) with 1,3‐diphenyl‐2‐(3‐vinylbenzyl)isothiourea ( 4 ) by use of dicyclohexylcarbodiimide (DCC). Homopolymerization of 6 led to new polystyrene derivatives ( 7 ) with mesoionic 4,6‐dioxo‐1,3‐diazines as pendant groups. UV irradiation of 7 yielded polystyrene derivatives with bis(β‐lactam) moieties as pendant groups ( 8 ). The change of some physical properties during the irradiation is discussed. 5‐Heptyl‐4,6‐dioxo‐1,3‐diphenyl‐2‐(3‐methylbenzylthio)‐1,3‐diazine ( 11 ) and 4‐heptyl‐1‐(3‐methylbenzylthio)‐3,5‐dioxo‐2,6‐diphenyl‐2,6‐diazabicyclo[2.2.0]hexane ( 12 ) as low‐molecular‐weight model compounds were synthesized for structural analysis.