Ring Expansions of Oxetanes

doi:10.6023/cjoc202008046

Abstract

Oxetanes are a class of important small heterocycles and intermediates in organic synthesis and have been widely applied in organic, pharmaceutical and polymer chemistries. As small heterocycles with a large ring tension, oxetanes not only prefer ring-opening reactions, but also favor ring expansions, to construct oxygen-containing common to large heterocyclic compounds. The ring expansion reactions of oxetanes, including the ring expansions with diazo compounds as carbene precursors, the metal catalyzed intermolecular cycloadditions and the intramolecular cycloadditions involving neighboring group participation, the nucleophilic ring expansion and so on are reviewed. Some reaction mechanisms of ring expansion reactions are analyzed, and new prospects for the future development of the ring expansion reactions are put forward.

Key words: oxetane, ring expansion, carbene, cycloaddition, nucleophilic reaction

Cite this article

Wenhao Yuan, Jiaxi Xu. Ring Expansions of Oxetanes[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 947-958.

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Fig. & Tab. 35

Scheme 1. Reaction of 2-phenyloxetane with methyl diazoacetate

Scheme 2. Ring expansion of oxetanes catalyzed by CuOTf and chiral bipyridyl

Scheme 3. Ring expansion of oxetanes catalyzed by CuOTf and bisazaferrocene

Scheme 4. Ring expansion of oxetane catalyzed by Cu(tfacac)2

Scheme 5. Photocatalytic ring expansion reaction of oxetanes

Scheme 6. Reaction mechanism of the photocatalytic ring expansion of oxetane

Scheme 7. Ru-catalyzed reaction of diazoketoesters with oxetanes

Scheme 8. Reaction mechanism of Ru-catalyzed ring expansion reaction

Scheme 9. Reaction of α-diazo-β-oxoalkanoates with oxetanes

Scheme 10. Reaction of diazonaphthoquinones with oxetane

Scheme 11. Formation of metallocarbenes from N-sulfonyl- triazoles

Scheme 12. Reaction of sulfonyltriazoles with 3,3-dimethyl- oxetane at low concentration

Scheme 13. Reaction of sulfonyltriazoles with 3,3-dimethyl- oxetane at high concentration

Scheme 14. Reaction of methanesulfonyl triazoles with 3,3- dimethyloxetane

Scheme 15. Reaction mechanism of sulfonyltriazoles with oxetane

Scheme 16. Reactions of vinyloxetanes with carbodiimides and isocyanates

Scheme 17. Reaction of silyl enol ethers with oxetane

Scheme 18. Reaction of N-alkynylamides with oxetanes

Scheme 19. Reaction of tert-butyl propiolates with oxetanes

Scheme 20. Reaction of azadienes with vinyloxetanes

Scheme 21. Reaction of formaldehyde with 2-vinyloxetanes

Scheme 22. Reaction of benzoxazinones with vinyloxetanes

Scheme 23. Cu-catalyzed intramolecular ring expansion of vinyloxetanes

Scheme 24. Cu(I)-catalyzed ring expansions of 2-ethynyl- oxetane to dihydrofuran-2-carbaldehydes and six-membered lactones

Scheme 25. Reactions of oxetane with CO2 and isocyanates

Scheme 26. Reactions of oxetane with ketene

Scheme 27. Cr-Salen complex-catalyzed reaction of oxetane and CO2

Scheme 28. Reaction of oxetane and CO2 catalyzed by VO(acac)2

Scheme 29. Iron amino triphenolate complex-catalyzed reaction of oxetane and CO2

Scheme 30. Reaction of oxetane and CO2 catalyzed by aluminum amino triphenolate complex

Scheme 31. Reaction of polysubstituted oxetane and CO2 catalyzed by aluminum amino triphenolate complex

Scheme 32. Electrocatalytic reaction of oxetane and CO2

Scheme 33. Reaction of oxetane and CO2

Scheme 34. Ring expansion reaction of sulfur ylide and oxetanes

Scheme 35. Ring expansion reaction of benzamides and oxetanes

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