Chemoselective aryl alkyl ether cleavage by thiophenolate anion through its in situ generation in catalytic amount

被引:56
作者
Nayak, MK
Chakraborti, AK
机构
[1] UNIV BURDWAN GOLAPBAG,DEPT CHEM,BURDWAN 713104,W BENGAL,INDIA
[2] NATL INST PHARMACEUT EDUC & RES,DEPT MED CHEM,SAS NAGAR 160062,INDIA
关键词
D O I
10.1016/S0040-4039(97)10342-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytically in situ generated alkali metal thiophenoxide in NMP (1-methyl-2-pyrrolidinone) chemoselectively cleaves aryl alkyl ethers in high yields. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8749 / 8752
页数:4
相关论文
共 27 条
[1]  
BEILY M, 1989, J ORG CHEM, V54, P2642
[2]   CLEAVAGE OF ETHERS [J].
BHATT, MV ;
KULKARNI, SU .
SYNTHESIS-STUTTGART, 1983, (04) :249-282
[3]   ALKYL THIOETHER ACTIVATION OF THE NITRO DISPLACEMENT BY ALKANETHIOL ANIONS - USEFUL PROCESS FOR THE SYNTHESIS OF POLY[(ALKYLTHIO)BENZENES] [J].
COGOLLI, P ;
TESTAFERRI, L ;
TINGOLI, M ;
TIECCO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2636-2642
[4]   NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTIONS OF UNACTIVATED ARYL HALIDES WITH THIOLATE IONS IN HEXAMETHYLPHOSPHORAMIDE [J].
COGOLLI, P ;
MAIOLO, F ;
TESTAFERRI, L ;
TINGOLI, M ;
TIECCO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2642-2646
[5]   REGIOSELECTIVITY IN THE ALKALINE THIOLATE DEPROTECTION OF ARYL METHYL ETHERS [J].
DODGE, JA ;
STOCKSDALE, MG ;
FAHEY, KJ ;
JONES, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :739-741
[6]  
FEUTRILL GI, 1970, TETRAHEDRON LETT, P1327
[7]  
Green T., 1991, PC User
[8]  
HANSSON C, 1976, SYNTHESIS-STUTTGART, P191
[9]   SYNTHESIS OF BOTH ENANTIOMERS OF NABILONE FROM A COMMON INTERMEDIATE - ENANTIODIVERGENT SYNTHESIS OF CANNABINOIDS [J].
HUFFMAN, JW ;
JOYNER, HH ;
LEE, MD ;
JORDAN, RD ;
PENNINGTON, WT .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2081-2086
[10]   Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor [J].
Huffman, JW ;
Yu, S ;
Showalter, V ;
Abood, ME ;
Wiley, JL ;
Compton, DR ;
Martin, BR ;
Bramblett, RD ;
Reggio, PH .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (20) :3875-3877