153446-20-9

Upstream product

• 107175-53-1 Methanesulfonic acid 3-(2-methylene-cyclohexyl)-propyl ester 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 108-94-1 cyclohexanone 
• 1126-19-8 2-(3'-chloropropyl)cyclohexanone 
• 4095-02-7 3-(2-oxocyclohexyl)propionic acid ethyl ester 
• 52890-22-9 ethyl 3-(2-methylidenecyclohexyl)propionate 
• 52890-23-0 2-(3-hydroxypropyl)methylenecyclohexane 
• 316147-63-4 2-(3-chloropropyl)methylenecyclohexane 

Relevant academic research and scientific papers

Epoxide-Initiated Cationic Cyclization of Azides: A Novel Method for the Stereoselective Construction of 5-Hydroxymethyl Azabicyclic Compounds and Application in the Stereo- and Enantioselective Total Synthesis of (+)- and (-)-Indolizidine 167B and 209D

A novel and general method has been developed for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide-initiated cationic cyclization of azides. The key cyclization reaction was systematically studied with the mo

Epoxide-initiated electrophilic cyclization of azides: A novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (±)-indolizidine 167B and 209D

(Matrix presented) A novel and general method for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide initiated electrophilic cyclization of azides has been developed and applied in the synthesis of (±)-indolizi

Azidomercurations of alkenes: Mercury-promoted Schmidt reactions

Azides bearing a suitably disposed alkene, when treated with either mercuric perchlorate or mercuric trifluoromethanesulfonate, produce bicyclic iminium ions. This new version of the Schmidt reaction proceeds by capture of the mercuronium ion intermediate by the azide to produce an aminodiazonium ion, which suffers a 1,2-shift to give an iminium ion (e.g., 10 → 16 → 17 → 18). Reduction of the iminium ion may then be carried out to produce an amine. Compared to earlier work on the protic acid-promoted intramolecular Schmidt reaction of azido-alkenes, the mercury-promoted Schmidt reaction has several advantages. First, the acid-promoted Schmidt reaction of azido-alkenes requires that the intermediate carbocations be tertiary, allylic, benzylic, or propargylic. The mercury-promoted method has no such limitation; thus even 1,2-disubstituted alkenes may be used. Second, the mercury-promoted method is milder, allowing the presence of acid-sensitive functionality. The protic version, typically employing trifluoromethanesulfonic acid, is limited in its functional group tolerance. Third, whereas carbocation rearrangement is often observed prior to cyclization/rearrangement in the acid-promoted Schmidt reaction, the mercury-promoted method avoids this problem. Fourth, the presence of the mercurio group during the rearrangment may alter the regioselectivity of the 1,2-migration. Finally, the mercury-bearing iminium ions that are the result of the Schmidt reaction were found to be sensitive to protodemercuration, precluding their use in other transformations.

Intramolecular schmidt reactions of azides with carbocations: Synthesis of bridged-bicyclic and fused-bicyclic tertiary amines

Aliphatic azides were captured intramolecularly by carbocations, producing aminodiazonium ion intermediates. Carbon-to-nitrogen rearrangement then occurred, generating bridged- or fused-bicyclic α-amino carbocations or iminium ions, depending on the geome