124920-20-3

Upstream product

• 65588-63-8 4-methyl-N-(6-methylheptan-2-yl)benzenesulfonamide 
• 913539-58-9 N-(1,5-dimethylhex-4-en-1-yl)(4-methylphenyl)sulfonamide 
• 22462-79-9 6-methylhept-5-en-2-amine 
• 22418-73-1 6-methylhept-5-en-2-one oxime 
• 110-93-0 6-Methyl-hept-5-en-2-on 

Relevant academic research and scientific papers

Piperidines from acid-catalysed cyclisations: Pitfalls, solutions and a new ring contraction to pyrrolidines

The success of acid-catalysed cyclisations of alka-4-enylamine derivatives to piperidines depends very much on the nature of the amine protecting group: while carbamates and related amides can usually be readily and cleanly transformed, the corresponding sulfonamides react further by ring contraction leading to pyrrolidines, especially when such substrates are sterically crowded.

Electroorganic chemistry. 120. New patterns of anodic oxidation of amides. Synthesis of α-amino aldehyde acetals and pyrrolidines from amines

Anodic oxidation of N-alkyltosylamides 1 in methanol containing KX (X = Br, I) gave two types of products, α-(tosylamino) aldehyde acetals 2 and pyrrolidine derivatives 3, and each of the products could selectively be formed by modifying the reaction conditions when the alkyl group on the nitrogen of 1 was not branched at its α-position. Namely, anodic oxidation ot N-(α-unbranched alkyl)tosylamides 1a-g in methanol containing NaOMe and KI at -10°C followed by further anodic oxidation at 25°C afforded 2 in good yields, while that of 1 in a two-layer system consisting of cyclohexane and water containing KOH and KBr under heating yielded solely 3. On the other hand, N-(α-branched alkyl)tosylamides 1h-j gave always 3. Two types of reaction routes leading to each of the products were proposed.