Designing Donor‐Acceptor Cyclopropane for the ThermalSynthesis of Carbocyclic Eight‐Membered Rings. Issue 7 (24th March 2023)

• Record Type: Journal Article
• Authors: Masson, Kévin; Dousset, Maxime; Biletskyi, Bohdan; Chentouf, Sara; Naubron, Jean‐Valère; Parrain, Jean‐Luc; Commeiras, Laurent; Nava, Paola; Chouraqui, Gaëlle
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 7(2023)
• Page Start: 1002
• Page End: 1011
• Publication Date: 2023-03-24
• Subjects: Donor-Acceptor Cyclopropane -- Rearrangement -- Eight-membered ring -- Mechanistic studies; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202300015
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An access to functionalised eight‐membered carbocyclic ring compounds was developed by simply stirring an unusual vinylogous Donor‐Acceptor Cyclopropane (DAC) in boiling o ‐xylene. Both experimental and computational studies were performed to explain the diastereoselectivity/regioselectivity transfer observed and to provide an overall picture of the mechanism. Abstract :