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Updated: Oct 7, 2025
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Recent Advances in the Domain of Cyclic (Alkyl)(Amino) Carbenes
Saroj Kumar Kushvaha1, Ankush Mishra1, Herbert W Roesky2
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Abstract:
Isolation of cyclic (alkyl) amino carbenes (cAACs) in 2005 has been a major achievement in the field of stable carbenes due to their better electronic properties. cAACs and bicyclic(alkyl)(amino)carbene (BicAAC) in essence are the most electrophilic as well as nucleophilic carbenes are known till date. Due to their excellent electronic properties in terms of nucleophilic and electrophilic character, cAACs have been utilized in different areas of chemistry, including stabilization of low valent main group and transition metal species, activation of small molecules, and catalysis. The applications of cAACs in catalysis have opened up new avenues of research in the field of cAAC chemistry. This review summarizes the major results of cAAC chemistry published until August 2021.
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.