Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Hylden, Anne T; Uzelac, Eric J.; Ostojic, Zeljko; Wu, Ting; Sacry, Keely L; Sacry, Krista L; Lin, Xiao; Jones, T. Nicholas

doi:10.3762/bjoc.7.155

Cited by 2 publications

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“…Accordingly, the 3‐hexynoic acid chloride 180 which is generated from its acid 179 with the aid of oxalyl chloride is cyclized to 3‐chloro‐2‐cyclohexenone 181 upon in situ addition of indium(III) chloride as the Lewis acid catalyst. Further addition of alcohol nucleophiles results in the formation of the expected products, 3‐alkoxy‐2‐cyclohexenones 182 (Scheme ) …”

Section: As An Acid Activatormentioning

confidence: 99%

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Mohammadkhani

Heravi

2019

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Oxalyl chloride, (COCl)2, as an inexpensive commercially available chemical is one of the most versatile applicable organic reagents in chemical transformations. It is also employed extensively in various chemical industries. It is employed in various chemical transformations such as chlorination, oxidation, reduction, dehydration, decarboxylation, and formylation reactions as well as ring cleavage of epoxides. During the past decades, numerous procedures using (COCl)2 as reagent have been developed and published. However, its importance has largely been overlooked by the absence of a comprehensive review in chemical literature dealing with its application in organic transformations and its utilization in the chemical industry. This Review aims to provide an overview for the applications of oxalyl chloride in organic synthesis, including its physical properties, synthesis, as well as its unique roles as the reagent in organic reactions, covering the literature over the past 103 years (from 1916 to date).

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Section: As An Acid Activatormentioning

confidence: 99%

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Mohammadkhani

Heravi

2019

ChemistrySelect

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Dimethylzinc‐Mediated Chlorolactamization of Homoallylic Amines with Chloroform

et al. 2015

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A novel chlorolactamization reaction of homoallylic amines has been developed. The treatment of homoallylic amines with dimethylzinc in chloroform led to the formation of the corresponding β‐chlorolactams via the Prins‐type cyclization of a carbamoyl chloride intermediate. The results of this study highlight the synthetic utility of chloroform as a source of both carbonyl group and chloride anion.

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Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Cited by 2 publications

References 10 publications

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Dimethylzinc‐Mediated Chlorolactamization of Homoallylic Amines with Chloroform

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Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Cited by 2 publications

References 10 publications

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Dimethylzinc‐Mediated Chlorolact­amization of Homoallylic Amines with Chloroform

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Dimethylzinc‐Mediated Chlorolactamization of Homoallylic Amines with Chloroform