Concise synthesis of chloro-benzoconduritols via effect of acetyl chloride (AcCl): Mattocks type reaction

Abstract

Concise and effective synthesis of novel halobenzoconduritols by the action of acetyl chloride is reported. Interesting monochloride and dichloride products are formed as a result of the reaction of benzoconduritol-D and 1,2,3,4-tetrahydro-1,4-epoxynaphthalene-2,3-diyl diacetate with acetyl chloride. We present surprising results bearing on the possible course and mechanism of the halobenzoconduritols synthesis. To the best of our knowledge, this reaction process represents the first example of the conversion of benzoconduritols to chloroesters. In terms of synthesis, the replacement of OH with halogen and its effects on neighboring groups were explained by the proposed mechanism (a Mattock-type mechanism).

Graphical Abstract

Keywords:

• Benzoconduritol-D
• effect of acetyl chloride
• halobenzoconduritols
• Mattock type reaction
• ring opening of bridged ether

Additional information

Funding

The authors are indebted to Ordu University Scientific Research Projects Coordination Unit [ODU/BAP, Grant No: A–2013] for financial support of this work.