CONVERSION OF AROMATIC KETONES, BENZYL ALCOHOLS, AND ALKYL ARYL ETHERS TO AROMATIC-HYDROCARBONS WITH LITHIUM 4,4'-DI-TERT-BUTYLBIPHENYL RADICAL-ANION

被引:12
作者
KARAMAN, R [1 ]
KOHLMAN, DT [1 ]
FRY, JL [1 ]
机构
[1] UNIV TOLEDO, DEPT CHEM, BOWMAN ODDY LABS, TOLEDO, OH 43606 USA
关键词
D O I
10.1016/S0040-4039(00)97012-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of tetrahydrofuran (THF) solutions of the title compounds with excess lithium (or potassium) metal under ultrasonic irradiation in the presence of catalytic amounts of the electron-transfer agent 4,4′-di-t-butylbiphenyl (DBB) caused conversions to aromatic hydrocarbons in good yields. Addition of 1 or 2 equiv of alkyl halides prior to aq ammonium chloride treatment during workup provided mono- or di-alkylated products. © 1990.
引用
收藏
页码:6155 / 6158
页数:4
相关论文
共 22 条
[1]  
ANDERSON EL, 1965, J ORG CHEM, P3959
[2]  
ASKINAZI BZ, 1967, RUSS J ORG CHEM+, V3, P353
[3]   UNSTABLE COMPOUNDS - SYNTHESIS AND EXPERIMENTAL AND COMPUTATIONAL STUDY OF THE CHEMICAL BEHAVIOR OF 9-[1-(2,4,6-CYCLOHEPTATRIENYL)]-9-XANTHYDROL [J].
BADEJO, IT ;
KARAMAN, R ;
FRY, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4591-4596
[4]   SYNTHESES OF 9-CYCLOHEPTA-2,4,6-TRIEN-1-YL-9H-XANTHEN-9-OL AND RELATED ALCOHOLS BY A NOVEL UMPOLUNG METHOD [J].
BADEJO, IT ;
KARAMAN, R ;
LEE, NWI ;
LUTZ, EC ;
MAMANTA, MT ;
FRY, JL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (09) :566-567
[5]   PHYSIOLOGICALLY ACTIVE COMPOUNDS .5. AMINOTHIOL ESTERS OF SUBSTITUTED ACETIC, CHLOROACETIC, BENZILIC, AND RELATED ACIDS [J].
BUEHLER, CA ;
KRYGER, AC ;
THAMES, SF ;
SMITH, HA ;
WELLS, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 1963, 6 (03) :230-&
[6]   ALKYLLITHIUM REAGENTS FROM ALKYL-HALIDES AND LITHIUM RADICAL-ANIONS [J].
FREEMAN, PK ;
HUTCHINSON, LL .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) :1924-1930
[7]  
FREEMAN PK, 1976, TETRAHEDRON LETT, P1849
[8]  
HALL SS, 1971, TETRAHEDRON LETT, P1853
[9]   LITHIUM-AMMONIA REDUCTION OF BENZALDEHYDES TO TOLUENES [J].
HALL, SS ;
ENGMAN, AM ;
BARTELS, AP .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (05) :760-+
[10]   LITHIUM-AMMONIA REDUCTION OF AROMATIC KETONES TO AROMATIC HYDROCARBONS [J].
HALL, SS ;
LIPSKY, SD ;
MCENROE, FJ ;
BARTELS, AP .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (18) :2588-&