Abstract
Abstract Reaction of 2-(3-methyl-2-butenyl)phenol (1) with PdCl2 gives 2,2-dimethylchromene (3) and 2,2-dimethyl-4-methoxychroman (4) (six-membered products) predominantly, together with trace amounts of 2-isopropylbenzofuran (5) and 2-isopropenyl-2,3-dihydrobenzofuran (6) (five-membered products). The reaction involves attack of the oxygen atom of the phenoxyl group at 2- or 3-position of the allylic side chain. Addition of various sodium carboxylates to the reaction mixture changes the regioselectivity. In the presence of sodium salts of carboxylic acids bearing electron-releasing substituents, nearly equal amounts of five and six-membered products are formed. The presence of sodium salts of carboxylic acids bearing electron-withdrawing substituents results in the predominant formation of the six-membered products. These results are discussed en the basis of alternation of reactive Pd(II) species. Results obtained from 2-(2-butenyl)phenol (2) are also reported.
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.
