Conversion of Alcohols, Thiols, Carboxylic Acids, Trimethylsilyl Ethers, and Carboxylates to Thiocyanates with Triphenylphosphine/Diethylazodicarboxylate/NH4SCN (original) (raw)

Preparation of Thiocyanates and Isothiocyanates from Alcohols, Thiols, Trimethylsilyl-, and Tetrahydropyranyl Ethers Using Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ)/n-Bu4NSCN System

ChemInform, 2006

A combination of triphenylphosphine (PPh 3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) provides a safe and easily available mixed reagent system for the conversion of 1 and 2 alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers to their corresponding thiocyanates and the 3 ones to isothiocyanates in good to high yields.

Conversion of Alcohols, Thiols, and Trimethysilyl Ethers to AlkyCyanides Using Triphenylphosphine

Journal of Organic Chemistry, 2004

Triphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone afford an adduct, which in the presence of n-Bu 4 NCN converts alcohols, thiols, and trimethylsilyl ethers into their corresponding alkyl cyanides in good to excellent yields at room temperature. This method is highly selective for the conversion of 1°alcohols in the presence of 2°and 3°ones, thiols and silyl ethers.

Conversion of Alcohols, Thiols, and Trimethysilyl Ethers to Alkyl Cyanides Using Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzoquinone/ n -Bu 4 NCN

The Journal of Organic Chemistry, 2004

Triphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone afford an adduct, which in the presence of n-Bu 4 NCN converts alcohols, thiols, and trimethylsilyl ethers into their corresponding alkyl cyanides in good to excellent yields at room temperature. This method is highly selective for the conversion of 1°alcohols in the presence of 2°and 3°ones, thiols and silyl ethers.

Conversion of Alcohols, Thiols, and Trimethysilyl Ethers to Alkyl Cyanides Using Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzoquinone/n-Bu4NCN

Journal of Organic Chemistry, 2004

Triphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone afford an adduct, which in the presence of n-Bu 4 NCN converts alcohols, thiols, and trimethylsilyl ethers into their corresponding alkyl cyanides in good to excellent yields at room temperature. This method is highly selective for the conversion of 1°alcohols in the presence of 2°and 3°ones, thiols and silyl ethers.

A novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the triphenylphosphine/2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ)/< i> n-Bu< sub> 4 NN< sub> 3 system

2004

Alkyl nitrites were prepared in good to excellent yields by treatment of alcohols, thiols and trimethylsilyl ethers with 2,4,6-trichloro[1,3,5]triazine/n-Bu 4 NNO 2 in refluxing acetonitrile. This method is highly selective for the conversion of primary alcohols to alkyl nitrites in the presence of secondary and tertiary alcohols, thiols and trimethylsilyl ethers.