168916-97-0

Basic information

• Product Name: 4-acetoxy-2,3-dimethyl-4-[4'-(tri-n-butylstannyl)phenyl]-2-cyclobutenone
• CAS NO: 168916-97-0
• Molecular Weight: 519.312
• Mol File: 168916-97-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-acetoxy-2,3-dimethyl-4-[4'-(tri-n-butylstannyl)phenyl]-2-cyclobutenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-acetoxy-2,3-dimethyl-4-[4'-(tri-n-butylstannyl)phenyl]-2-cyclobutenone(168916-97-0)
• EPA Substance Registry System: 4-acetoxy-2,3-dimethyl-4-[4'-(tri-n-butylstannyl)phenyl]-2-cyclobutenone(168916-97-0)

Safety Data

• Hazardous Substances Data: 168916-97-0(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 1121-15-9 3,4-dimethylcyclobut-3-ene-1,2-dione 

Relevant articles and documents

General synthetic entry to highly-oxygenated, angularly-fused polycyclic aromatic compounds

A convergent and efficient synthesis of highly-oxygenated, angularly-fused polycyclic aromatic compounds has been developed. Nucleophilic addition of [4-(tri-n-butylstannyl)phenyl]lithium to a 3,4-disubstituted-cyclobutene-1,2-dione followed by appropriate protection of the hydroxyl group and thermal rearrangement of the O-protected addition product generated a 1,4-dioxygenated-2,3-disubstituted-6-(tri-n-butylstannyl)naphthalene. Stille coupling of the 6-(tri-n-butylstannyl)naphthalene with a 4-chloro-2,3-disubstituted-2-cyclobutenone and thermolysis of the coupled product gave highly-oxygenated phenanthrenes. An isomeric series of compounds was generated from [3-(tri-n-butylstannyl)phenyl]lithium. Substituted phenanthrenes at higher overall levels of oxygenation were prepared by (1) thermolysis of the adduct obtained by addition of a lithiated naphthalene, generated by Sn → Li exchange from a 1,4-dioxygenated-2,3-disubstituted-6-(tri-n-butylstannyl)naphthalene, to a cyclobutenedione or (2) thermolysis of the double adducts generated by reaction of 2 equiv of a cyclobutenedione with either 1,4-dilithiobenzene or 1,3-dilithiobenzene. Phenanthrenes at lower levels of oxygenation were prepared by the palladium-catalyzed cross-coupling/thermolysis of 2 equivalents of a 4-chlorocyclobutenone with either 1,4-bis(tri-n-butylstannyl)benzene or 1,3-bis(tri-n-butylstannyl)benzene.