Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

Sun, Wei; Kayal, Surajit; Raimbach, William A. T.; Sun, Xue Zhong; Light, Mark E.; Hanson-Heine, Magnus W. D.; George, Michael W.; Harrowven, David C.

Abstract

Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heterocycles show the value of the methods, while TA-spectroscopy and TD-DFT studies provide mechanistic insights on their wavelength dependence.

Citation

Sun, W., Kayal, S., Raimbach, W. A. T., Sun, X. Z., Light, M. E., Hanson-Heine, M. W. D., George, M. W., & Harrowven, D. C. (2022). Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides. Chemical Communications, 58(10), 1546-1549. https://doi.org/10.1039/d1cc06800h

• Journal Article Type: Article
• Acceptance Date: Dec 23, 2021
• Online Publication Date: Dec 23, 2021
• Publication Date: Feb 4, 2022
• Deposit Date: Jan 26, 2022
• Publicly Available Date: Jan 26, 2022
• Journal: Chemical Communications
• Print ISSN: 1359-7345
• Electronic ISSN: 1364-548X
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 58
• Issue: 10
• Pages: 1546-1549
• DOI: https://doi.org/10.1039/d1cc06800h
• Keywords: Materials Chemistry; Metals and Alloys; Surfaces, Coatings and Films; General Chemistry; Ceramics and Composites; Electronic, Optical and Magnetic Materials; Catalysis
• Public URL: https://nottingham-repository.worktribe.com/output/7340486
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2022/CC/D1CC06800H