An Efficient Route to Alkyl Chlorides from Alcohols Using the Complex TCT/DMF

Luca, Lidia De; Giacomelli, Giampaolo; Porcheddu, Andrea

doi:10.1021/ol017168p

Cited by 138 publications

(76 citation statements)

References 18 publications

(19 reference statements)

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“…33 and acyl azides. 34 In order to optimize the reaction conditions, at first the effect of different molar ratios of ROH/TT/n-Bu 4 our optimized conditions for the conversion of structurally different alcohols into their corresponding alkyl azides with 100% conversion (substrate consumption) which determined by GC.…”

Section: Resultsmentioning

confidence: 99%

A Novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the 2,4,6-trichloro[1,3,5]triazine/n-Bu4NN3 system

Akhlaghinia¹,

Samiei²

2007

J. Braz. Chem. Soc.

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Alquil azidas são preparadas em bons a excelentes rendimentos, pelo tratamento de álcoois, tióis e trimetilsilil éteres com 2,4,6-tricloro[1,3,5]triazina/n-Bu 4 NN 3 em acetonitrila. Este método é altamente seletivo para conversão de álcoois primários a alquil azidas na presença de álcoois secundários e terciários, tióis e trimetilsilil éteres.Alkyl azides are 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 NN 3 in acetonitrile. This method is highly selective for conversion of primary alcohols to alkyl azides in the presence of secondary and tertiary alcohols, thiols and trimethysilyl ethers.

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Section: Resultsmentioning

confidence: 99%

A Novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the 2,4,6-trichloro[1,3,5]triazine/n-Bu4NN3 system

Akhlaghinia¹,

Samiei²

2007

J. Braz. Chem. Soc.

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“…Um método eficiente para esta transformação química foi descrito por Giacomelli e colaboradores 35 , que empregaram a reação entre álcoois primários ou secundários e um complexo do tipo Vilsmeier-Haack (56), levando à formação das espécies catiônicas 59a-c as quais, subseqüentemente, são transformadas nos cloretos de alquila 60a-c correspondentes, através de reação com íon cloreto (Esquema 13).…”

Section: Preparação De Derivados Cloradosunclassified

Cloreto isocianúrico e cloreto cianúrico: aspectos gerais e aplicações em síntese orgânica

Cunha¹,

Paixão²,

Souza³

et al. 2006

Quím. Nova

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Recebido em 10/2/05; aceito em 13/7/05; publicado na web em 8/2/06 ISOCYANURIC CHLORIDE ACID AND CYANURIC CHLORIDE: GENERAL ASPECTS AND APPLICATIONS IN ORGANIC SYNTHESIS. The aromatic six-membered heterocycles having three nitrogen atoms are denominated triazines. Among these heterocycles, isocyanuric chloride and cyanuric chloride are inexpensive and readily available 1,3,5-triazine derivatives, which have been attracting significant attention of organic chemists due to their different kinds of applications, which vary from pharmaceuticals to explosives. This short overview explores their uses in synthetic methods, as chlorinating and oxidating agents and some procedures for their preparation.

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“…This procedure can also be applied to optically active carbinols. 19 (E) Efficient conversion of primary alcohols to the corresponding formate esters can be carried out at room temperature in methylene chloride, using cyanuric chloride and N,N-dimethyl formamide in the presence of lithium fluoride. This is a useful method for selectively protecting primary hydroxyl groups.…”

Section: Abstractsmentioning

confidence: 99%