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The Willgerodt-Kindler Reaction in Water: High Chemoselectivity of Benzaldehydes over Acetophenones

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Summary.

Water has been found for the first time as a useful solvent in the Willgerodt-Kindler (WK) reaction for the synthesis of benzothiomorpholides in high yield at 80°C for 3 h. This novel approach confronts the WK protocol with a new situation in which water not only is not regarded as a serious disadvantage but also is applied in this case as a useful solvent in the reaction. The basis of this finding is the presence of a methylene chain in the carbonyl substrates, which leads to the high reaction selectivity of benzaldehydes over acetophenones.

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Authors and Affiliations

  1. Chemistry & Chemical Engineering Research Center of Iran, Tehran, Iran

    Kioumars Aghapoor, Farshid Mohsenzadeh, Golriz Khanalizadeh & Hossein R. Darabi

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  1. Kioumars Aghapoor
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  2. Farshid Mohsenzadeh
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  3. Golriz Khanalizadeh
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  4. Hossein R. Darabi
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Correspondence to Hossein R. Darabi.

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Aghapoor, K., Mohsenzadeh, F., Khanalizadeh, G. et al. The Willgerodt-Kindler Reaction in Water: High Chemoselectivity of Benzaldehydes over Acetophenones. Monatsh. Chem. 138, 61–65 (2007). https://doi.org/10.1007/s00706-006-0560-7

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  • DOI: https://doi.org/10.1007/s00706-006-0560-7

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