One‐pot Construction of Dibenzooxabicyclo[5.5.0]dodecanes

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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-12, Vol.364 (23), p.4110-4121
Main Authors: Hsueh, Nai‐Chen, Chen, Kuan‐Ting, Chang, Meng‐Yang
Format: Article
Language:English
Subjects:
Alkylation
Annulation
Nucleophilic substitution
One-pot reaction
Polycycles
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200914