Cycloaddition reactions of o-quinone methides with polarized olefins. (April 2021)

• Record Type: Journal Article
• Authors: Osyanin, Vitaly A.; Lukashenko, Anton V.; Osipov, Dmitry V.
• Is Part Of: Russian chemical reviews. Volume 90:Number 3(2021)
• Page Start: 324
• Page End: 373
• Publication Date: 2021-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1070/RCR4971
• Languages: English
• ISSNs: 0036-021X

Abstract

Abstract : The review summarizes and systematizes the [4+2]-cycloaddition reactions of o -quinone methides with electron-rich and electron-deficient olefins. The electron-rich substrates include vinyl ethers, vinyl sulfides, enamines, enamides, enols, furans, benzofurans and indoles, while the electron-deficient substrates are esters of unsaturated carboxylic acids, vinyl azides and quinones. Reactions with push-pull and captodative olefins are also considered. The mechanisms of some reactions are presented. A separate part of the review addresses reactions of p -quinone methides containing an o -hydroxyphenyl substituent at the exocyclic carbon atom, which can isomerize to o -quinone methides. Much attention is paid to oligomerization of o -quinone methides, which proceeds in the absence of active dienophiles or nucleophiles. The bibliography includes 217 references.