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One-pot Construction of Dibenzooxabicyclo[5.5.0]dodecanes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-10-21 , DOI: 10.1002/adsc.202200914
Nai-Chen Hsueh, Kuan-Ting Chen, Meng-Yang Chang

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.

中文翻译:

二苯并氧双环[5.5.0]十二烷的一锅法构建

在敞开容器气氛条件下,一锅法合成双磺酰基二苯并氧杂双环[5.5.0 ]十二。得到 1,3-双磺酰基丙酮和 2 当量的-双(溴甲基)芳烃。提出并讨论了一种合理的机制。这种高产方案通过形成三个碳-碳单 (C-C) 键、两个碳-硫单 (C-S) 键和一个碳-氧单键 ( C−O) 债券。
更新日期:2022-10-21
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