24767-72-4

Basic information

• Product Name: penta-3,4-dien-1-yl 4-bromobenzenesulfonate
• CAS NO: 24767-72-4
• Molecular Weight: 303.177
• Mol File: 24767-72-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: penta-3,4-dien-1-yl 4-bromobenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: penta-3,4-dien-1-yl 4-bromobenzenesulfonate(24767-72-4)
• EPA Substance Registry System: penta-3,4-dien-1-yl 4-bromobenzenesulfonate(24767-72-4)

Safety Data

• Hazardous Substances Data: 24767-72-4(Hazardous Substances Data)

Upstream product

• 1387576-58-0 pent-4-yn-1-yl 4-bromobenzenesulfonate 
• 5390-04-5 pent-1-yn-5-ol 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 5557-88-0 pent-2-en-4-yn-1-ol 
• 5557-87-9 3,4-pentadiene-1-ol 

Relevant articles and documents

Cyclization of gold acetylides: Synthesis of vinyl sulfonates via gold vinylidene complexes

Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β-carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold-catalyzed reactions, but for the new substrates, only one gold atom is needed for substrate activation. After formation of a gold vinylidene complex, which forms a tight contact ion pair with the sulfonate leaving group, recombination of the two parts delivers vinyl sulfonates, which are valuable targets that can serve as precursors for cross-coupling reactions, for example. Gold vinylidene intermediates are generated by the cyclization of gold acetylides that carry a sulfonate leaving group. This result demonstrates for the first time that the formation of these species is not restricted to a dual activation mode. The cyclization products obtained herein contain a vinyl sulfonate moiety, which makes them useful building blocks for cross-coupling reactions.