Precursors to the cyclo(n)carbons: From 3,4-dialkynyl-3-cyclobutene-1,2-diones and 3,4-dialkynyl-3-cyclobutene-1,2-diols to cyclobutenodehydroannulenes and higher oxides of carbon
- Univ. of California, Los Angeles (USA)
A series of novel cyclobutenodehydro(n)annulenes (n = 18, 24, 30) have been prepared as precursors in an organic approach to the cyclocarbons C{sub 18}, C{sub 24}, and C{sub 30}. On the way to these macrocycles, synthetic entries to three new classes of enediynes have been developed. Bis(1-propynyl)cyclopropenone was prepared in the reaction of 1-(trimethylsilyl)-1-propyne with trichlorocyclopropenylium tetrachloroaluminate. The 3,4-dialkynyl-3-cyclobutene-1,2-dionines were prepared by the reaction of 3,4-dichloro-3-cyclobutene-1,2-dione either with (tri-n-butylstannyl)alkynes in the presence of catalytic amounts of Pd(PPh{sub 3}){sub 4} or with the soluble copper (I) acetylides of (trialkylsilyl)acetylenes. The peculiar downfield resonances of the terminal acetylenic carbon atoms in the {sup 13}C NMR spectra of the 3,4-dialkynyl-3-cyclobutene-1,2-diones are discussed. The oxidative Hay coupling of the acetonide of 3,4-diethynyl-3-cyclobutene-1,2-diol or of the bis(ethylene ketal) of 3,4-diethynyl-3-cyclobutene-1,2-dione gave two series of cyclobutenodehydroannulenes with 18{pi}-, 24{pi}-, and 30{pi}-electron perimeters.
- OSTI ID:
- 6728394
- Journal Information:
- Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 112:4; ISSN 0002-7863; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
Similar Records
Molecular and crystal structure of squaric acid (3,4-dihydroxy-3-cyclobutene-1,2-dione) at 121 /sup 0/C: A neutron diffraction study
Electronic and structural properties of the cyclobutenodehydroannulenes
Related Subjects
360601* -- Other Materials-- Preparation & Manufacture
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
ALKANES
ALKENES
CALCULATION METHODS
CARBON COMPOUNDS
CARBON OXIDES
CHALCOGENIDES
CHEMICAL PREPARATION
CYCLOALKANES
CYCLOALKENES
DATA ANALYSIS
HYDROCARBONS
MEASURING INSTRUMENTS
MEASURING METHODS
ORGANIC COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
SYNTHESIS