Interesting Reactivity in the Thermolysis and Photolysis of 2,3-Diphenyl-1-naphthol

Autor: Lara C. Spencer, S. V. Shorunov, Howard E. Zimmerman, Ilia A. Guzei
Rok vydání: 2008
Předmět:
Zdroj: Journal of Chemical Crystallography. 39:399-406
ISSN: 1572-8854
1074-1542
Popis: 2,3-Diphenyl-1-naphthol (1) undergoes two unexpected reactions under different conditions. Compound (1) was heated in DMSO-d6 and underwent a Pummerer type thermal reaction to give two isomeric products, 1-(methylthio)methoxy-2,3-diphenyl naphthol-d5 which crystallized in the space group $$ P{\bar{\text{1}}} $$ with a = 7.1610(9) A, b = 11.2795(15) A, c = 12.8905(17) A, α = 114.049(2)°, β = 96.589(2)°, and γ = 102.945(2)°, and 2-(methylthio)methyl-2,3-diphenyl 1(2H)-naphthalenone-d5 which crystallized in the space group $$ P{\bar{\text{1}}} $$ with a = 8.5981(5) A, b = 10.4374(6) A, c = 11.1078(6) A, α = 78.748(2)°, β = 67.709(2)°, and γ = 83.184(2)°. Photolysis (254 nm) of (1) resulted in 2,2′,3,3′-tetraphenyl-1,1′-bi-2-naphthol which crystallized in the space group P21/c with a = 26.3616(11) A, b = 10.1707(4) A, c = 23.3376(9) A, and β = 99.034(2)°. When 2,3-diphenyl-1-naphthol was heated in DMSO-d6 two unexpected isomers, 1-(methylthio)methoxy-2,3-diphenyl naphthol-d5 and the racemate 2-(methylthio)methyl-2,3-diphenyl 1(2H)-naphthalenone-d5 were produced. Photolysis in THF at 254 nm led to the unexpected product 2,2′,3,3′-tetraphenyl-1,1′-bi-2-naphthol. All structures were elucidated by X-ray crystallography.
Databáze: OpenAIRE
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