477977-14-3

Basic information

• Product Name: Benzenesulfonamide, N-(1-cyclopenten-1-ylmethyl)-4-methyl-N-2-propynyl-
• CAS NO: 477977-14-3
• Molecular Formula: C16H19NO2S
• Molecular Weight: 289.398
• Mol File: 477977-14-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-(1-cyclopenten-1-ylmethyl)-4-methyl-N-2-propynyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(1-cyclopenten-1-ylmethyl)-4-methyl-N-2-propynyl-(477977-14-3)
• EPA Substance Registry System: Benzenesulfonamide, N-(1-cyclopenten-1-ylmethyl)-4-methyl-N-2-propynyl-(477977-14-3)

Safety Data

• Hazardous Substances Data: 477977-14-3(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 1120-80-5 cyclopent-1-ene-1-methanol 
• 1560-11-8 cyclopent-1-enecarboxylic acid 
• 69543-15-3 1-bromomethylcyclopentene 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 

Relevant articles and documents

Tandem ring-opening/ring-closing metathesis polymerization: Relationship between monomer structure and reactivity

Monomers containing either cycloalkenes with low ring strain or 1-alkynes are poor monomers for olefin metathesis polymerization. Ironically, keeping two inactive functional groups in proximity within one molecule can make it an excellent monomer for metathesis polymerization. Recently, we demonstrated that monomer 1 having cyclohexene and propargyl moieties underwent rapid tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization via relay-type mechanism. Furthermore, living polymerization was achieved when a third-generation Grubbs catalyst was used. Here, we present a full account on this tandem polymerization by investigating how various structural modifications of the monomers affected the reactivity of the tandem polymerization. We observed that changing the ring size of the cycloalkene moieties, the length of the alkynes, and linker units influenced not only the polymerization rates but also the reactivities of Diels-Alder reaction, which is a post-modification reaction of the resulting polymers. Also, the mechanism of tandem polymerization was studied by conducting end-group analysis using 1H NMR analysis, thereby concluding that the polymerization occurred by the alkyne-first pathway. With this mechanistic conclusion, factors responsible for the dramatic structure-reactivity relationship were proposed. Lastly, tandem RO/RCM polymerization of monomers containing sterically challenging trisubstituted cycloalkenes was successfully carried out to give polymer repeat units having tetrasubstituted cycloalkenes.

Ruthenium-Catalyzed ROM-RCM of Cycloalkene-yne

(Matrix Presented) ROM-RCM (ring-opening and ring-closing metatheses) of cycloalkene-yne was demonstrated using a second-generation ruthenium complex. When cycloalkene bearing the alkyne moiety at the C-1 position was reacted with a ruthenium-carbene complex under an atmosphere of ethylene, ROM-RCM proceeded smoothly to give bicyclic compound and/or dimeric compound in good yields.