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Thione–Thiol Rearrangement: Miyazaki–Newman–Kwart Rearrangement and Others

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Sulfur-Mediated Rearrangements II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 275))

Abstract

Thione-to-thiol rearrangements represent a general route for the synthesis of sulfur compoundsfrom hydroxyl functionalities. In particular, the Miyazaki–Newman–Kwart rearrangementhas been widely used for the synthesis of aromatic thiols from the corresponding phenols.

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Abbreviations

DMF:

Dimethylformamide

DABCO:

1,4-Diazabiciclo[2.2.2]octane

DMAP:

Dimethylaminopyridine

DMTCl:

Dimethylthiocarbamoyl chloride

DETCl:

Diethylthiocarbamoyl chloride

PTC:

Phase transfer catalyst

BINOL:

Binaphthol

MOP:

2-(Diphenylphosphino)-2′-alkoxy-1,1′-binaphthyl

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Acknowledgments

This work was co-founded by MIUR within the PRIN national framework.

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Authors and Affiliations

  1. Dipartimento di Chimica, Università Ca' Foscari di Venezia, Dorsoduro 2137, 30123, Venezia, Italy

    Cristiano Zonta & Ottorino De Lucchi

  2. Zambon Group Spa, via Dovaro 2, 36045, Lonigo, Vicenza, Italy

    Raffaella Volpicelli & Livius Cotarca

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  1. Cristiano Zonta
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  2. Ottorino De Lucchi
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  3. Raffaella Volpicelli
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  4. Livius Cotarca
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Correspondence to Cristiano Zonta .

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Ernst Schaumann

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Zonta, C., De Lucchi, O., Volpicelli, R., Cotarca, L. (2006). Thione–Thiol Rearrangement: Miyazaki–Newman–Kwart Rearrangement and Others. In: Schaumann, E. (eds) Sulfur-Mediated Rearrangements II. Topics in Current Chemistry, vol 275. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_065

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