One‐pot Construction of Dibenzooxabicyclo[5.5.0]dodecanes. Issue 23 (11th November 2022)

• Record Type: Journal Article
• Authors: Hsueh, Nai‐Chen; Chen, Kuan‐Ting; Chang, Meng‐Yang
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 23(2022)
• Page Start: 4110
• Page End: 4121
• Publication Date: 2022-11-11
• Subjects: Alkylation -- Annulation -- One-pot reaction -- Nucleophilic substitution -- Polycycles; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200914
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Under the open‐vessel atmosphere conditions, the one‐pot synthesis of bis‐sulfonyl dibenzooxabicyclo[5.5.0]dodecanes was developed by double substitution of 1, 3‐dichloroacetone with arenesulfinic acid sodium salts, and C ‐ and O‐ alkylation of the resulting 1, 3‐bis‐sulfonylacetones with 2 equivalents of o ‐bis(bromomethyl)arenes. A plausible mechanism is proposed and discussed. This high‐yielding protocol provides an intermolecular substitution and an intramolecular ring‐closure via the formations of three carbon−carbon single (C−C) bonds, two carbon−sulfur single (C−S) bonds, and one carbon−oxygen single (C−O) bond. Abstract :