Influence of the Interaction between a Tin Catalyst and an Accelerator on the Formose‐Inspired Synthesis of α‐Hydroxy‐γ‐butyrolactone. Issue 7 (25th February 2016)

• Record Type: Journal Article
• Authors: Yamaguchi, Sho; Matsuo, Takeaki; Motokura, Ken; Miyaji, Akimitsu; Baba, Toshihide
• Is Part Of: ChemCatChem. Volume 8:Issue 7(2016)
• Page Start: 1386
• Page End: 1391
• Publication Date: 2016-02-25
• Subjects: domino reactions -- formaldehyde -- formose reaction -- homogeneous catalysis -- lactones; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201501377
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: In this study, we focused on the tin‐catalyzed transformation of formaldehyde into α‐hydroxy‐γ‐butyrolactone (HBL) in the presence of an α‐hydroxy carbonyl compound as the accelerator. The screening of various accelerators aided in clarifying the structural prerequisites of the accelerator for the formose‐inspired synthesis of HBL. To investigate the influence of the interactions between the tin metal and the accelerator on the catalytic activity, we performed a deuterium‐exchange experiment with α‐hydroxyacetophenone followed by in situ 119 Sn NMR spectroscopy and X‐ray absorption fine structure measurements. On the basis of the experimental results, we proposed a reaction mechanism to obtain HBL. Abstract : Party of four : The interaction between the tin catalyst and an accelerator on the formose‐inspired synthesis of α‐hydroxy‐γ‐butyrolactone (HBL) is examined. On the basis of the experimental results, we propose a reaction mechanism to obtain HBL through an aldol reaction and subsequent 1, 2‐hydride shift with a complex of the tin catalyst and the accelerator.