Abstract
The ring opening of two spiro-Meisenheimer complexes to give respectively 1-(2-hydroxyethoxy)-2,4,6-trinitrobenzene and 1-(2-hydroxyethoxy)-2,4-dinitronaphthalene is found to be subject to general acid catalysis in water. The α value of the Bronsted equation is 0·5. The isotope effect of the hydronium ion catalysed reaction KD3O+/KH3O+= 1·5. A mechanism is proposed involving concerted oxygen protonation and C–O bond breaking. The uncatalysed reaction is shown to proceed by a unimolecular mechanism rather than a bimolecular reaction with water. The results are compared with those for non-cyclic analogues.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
