ChemInform Abstract: A Convenient One‐Pot Synthesis of α‐Isothiocyanatoethers and Unusual Course of Some of Its Nucleophilic Displacement Reactions.

Bernát, Juraj; Kristián, Pavol; Guspanová, Jana; Imrich, Ján; Busova, T.

doi:10.1002/chin.199809070

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2012

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“…The X-pyridines (GR grade) were used without further purifications. The substrate was synthesized as previously mentioned way, 1,19 where ethyl dichlorophosphate (1.73 g; 0.01 mole) was taken into a round-bottomed flask with MeCN (25 mL) as solvent. Equivalent amount of potassium thiocyanate solution were taken into another flask with 25 mL MeCN.…”

Section: Methodsmentioning

confidence: 99%

Kinetics and Mechanism of the Pyridinolysis of Diethyl Isothiocyanophosphate in Acetonitrile

Adhikary¹,

Lee

2012

Bulletin of the Korean Chemical Society

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The kinetics and mechanism of the pyridinolysis (XC 5 H 4 N) of diethyl isothiocyanophosphate are investigated in acetonitrile at 55.0 o C. The Hammett and Brönsted plots for substituent X variations in the nucleophiles exhibit the two discrete slopes with a break region between X = 3-Ac and 4-Ac. These are interpreted to indicate a mechanistic change at the break region from a concerted to a stepwise mechanism with rate-limiting expulsion of the isothiocyanate leaving group from a trigonal bipyramidal pentacoordinated intermediate. The relatively large β X values with more basic and less basic pyridines imply much greater fraction of frontside nucleophilic attack TSf than that of backside attack TSb.

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Section: Methodsmentioning

confidence: 99%