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 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.

Automated summary

A high-yielding one-pot synthesis method for the bis-sulfonyl dibenzooxabicyclo[5.5.0]dodecanes has been developed under open-vessel atmosphere conditions. This method involves a double substitution reaction between 1,3-dichloroacetone and arenesulfinic acid sodium salts, followed by C- and O-alkylation of the resulting 1,3-bis-sulfonylacetones with o-bis(bromomethyl)arenes. The formation of three carbon-carbon single bonds, two carbon-sulfur single bonds, and one carbon-oxygen single bond contributes to the success of this protocol.