Abstract
When exposed to visible light, 2,5-di-tert-butyl-6-hydroxy-6-methylcyclohexa-2,4-dienone undergoes rearrangements in several steps. The first, photochemical step involves contraction of the six-membered ring to a five-membered cyclic ketol. Its subsequent rearrangements follow a number of parallel pathways. The main pathway involves the formation of an unstable intermediate bicyclo[3.1.0]hexenone derivative, whose further transformation leads to 4-acetylcyclopentenone via opening of the three-membered ring in a deaerated solution or to a bicyclic peroxide in the presence of air. In addition, a parallel bimolecular reaction of the five-membered ketol yields sterically hindered 2-acetylcyclopentenone.
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 callDisclaimer: 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.
