T3P® – A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates

Łukasz Janczewski; Anna Gajda; Sebastian Frankowski; Tomasz M. Goszczyński; Tadeusz Gajda

doi:10.1055/s-0036-1591842

Synthesis, Table of Contents

Synthesis 2018; 50(05): 1141-1151
DOI: 10.1055/s-0036-1591842

paper

T3P^® – A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates

Łukasz Janczewski

^aInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, 116 Stefan Żeromski St., 90-924 Lodz, Poland Email: tadeusz.gajda@p.lodz.pl

,

Anna Gajda

^aInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, 116 Stefan Żeromski St., 90-924 Lodz, Poland Email: tadeusz.gajda@p.lodz.pl

,

Sebastian Frankowski

^aInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, 116 Stefan Żeromski St., 90-924 Lodz, Poland Email: tadeusz.gajda@p.lodz.pl

,

Tomasz M. Goszczyński

^bDepartment of Experimental Oncology, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 Rudolf Weigl St., 53-114 Wrocław, Poland

,

Tadeusz Gajda *

^aInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, 116 Stefan Żeromski St., 90-924 Lodz, Poland Email: tadeusz.gajda@p.lodz.pl

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Abstract

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Abstract

A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41–94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P^® (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.

Key words

isothiocyanates - desulfuration - propane phosphonic acid anhydride (T3P^®) - dithiocarbamates - amino acids - amines

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References

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