Bicyclo[4.1.0]hepta-1,3,5-trien-7-one

Base Information

• Chemical Name: Bicyclo[4.1.0]hepta-1,3,5-trien-7-one
• CAS No.: 22406-98-0
• Molecular Formula: C7H4O
• Molecular Weight: 104.10600
• DSSTox Substance ID: DTXSID40583286
• Nikkaji Number: J1.476.355D
• Wikidata: Q82474825
• Mol file: 22406-98-0.mol

Synonyms:benzocyclopropenone;Bicyclo[4.1.0]hepta-1,3,5-trien-7-one;22406-98-0;SCHEMBL4311602;DTXSID40583286

Chemical Property of Bicyclo[4.1.0]hepta-1,3,5-trien-7-one

Chemical Property:

• PSA: 17.07000
• LogP: 1.07560
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 104.026214747
• Heavy Atom Count: 8
• Complexity: 114

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C2=O

Refernces

A photochemical synthesis of benzocyclopropenone

10.1039/C29690000220

The study investigates the photochemical synthesis of benzocyclopropenone (IVa) through the decomposition of lithium 3-p-tolyl sulphonylamino-1,2,3-benzotriazin-4(3H)-one (Ia) and its 6-chloro-analogue (Ib). The precursor compounds are prepared by diazotization of anthranilic acid toluene-sulfonohydrazides and subsequent treatment with lithium hydride or lithium methoxide. Upon UV excitation, Ia decomposes to yield lithium toluene-p-sulphonate, methyl benzoate, and o-methoxybenzoic acid toluene-p-sulphonohydrazide, while Ib gives lithium toluene-p-sulphonate, methyl p-chlorobenzoate, and 5-chloro-2-methoxy-benzoic acid toluene-p-sulphonohydrazide. The formation of p-chlorobenzoate suggests the involvement of a benzocyclopropenone intermediate (IVb) in the reaction mechanism, which undergoes hemiacetal formation and Favorskii ring-opening to produce the ester. The study also explores the thermolysis of Ia in triglyme, which yields triptycene, possibly via decarbonylation of IVa to form benzyne (VIIIa), and the photolysis of Ib in benzene, producing a small amount of p-chlorobenzophenone.