Home Chemistry Heterocyclic Building Blocks Aliphatic Heterocycles 3H-Diazirine
Ring Expansion: 3H-diazirine can undergo ring expansion reactions to form larger ring structures. For example, it can be converted into 1,2,3-triazole through ring expansion.
Cycloaddition Reactions: 3H-diazirine can participate in cycloaddition reactions with other molecules. For instance, it can undergo [2+1] cycloaddition reactions with various unsaturated compounds, forming new ring systems.
Nitrene Insertion: The nitrogen atom in 3H-diazirine can act as a nitrene precursor. Nitrenes are highly reactive intermediates that can insert into carbon-hydrogen bonds of other organic compounds, leading to the formation of new carbon-nitrogen bonds.
Photochemical Reactions: 3H-diazirine is particularly known for its photochemical reactivity. When exposed to UV light, it can undergo photochemical decomposition, leading to the formation of highly reactive carbene intermediates, which can participate in various reactions.
Electrophilic Addition: The strained nature of the 3H-diazirine ring makes it susceptible to electrophilic attack. It can react with electrophiles, such as halogens or Lewis acids, leading to the addition of these groups to the ring.
Rearrangements: In some cases, 3H-diazirine may undergo rearrangement reactions, leading to the formation of different isomeric products.
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2-(3-But-3-ynyl-3H-diazirin-3-yl)-ethanol
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3-(3-Methyl-3H-diazirine-3-yl)propionic acid
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2-(3-(But-3-yn-1-yl)-3H-diazirin-3-yl)ethan-1-amine
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2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]acetic acid
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2-(3-Methyl-3H-diazirin-3-yl)ethanamine
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3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine
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