OXIDATION OF DIPHENYL DISELENIDE WITH CERIC AMMONIUM-NITRATE - A NOVEL ROUTE FOR FUNCTIONALIZATION OF OLEFINS

被引:40
作者
BOSMAN, C [1 ]
DANNIBALE, A [1 ]
RESTA, S [1 ]
TROGOLO, C [1 ]
机构
[1] UNIV ROMA LA SAPIENZA,CNR,CTR STUDIO CHIM SOSTANZE ORGAN NAT,I-00185 ROME,ITALY
关键词
D O I
10.1016/S0040-4039(00)78263-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkenes were reacted with diphenyl diselenide in presence of eerie ammonium nitrate in methanol, affording beta-methoxyalkyl phenyl selenides in good yields.
引用
收藏
页码:6525 / 6528
页数:4
相关论文
共 11 条
[1]   SELENIUM-CATALYZED NONRADICAL CHLORINATION OF OLEFINS WITH N-CHLOROSUCCINIMIDE [J].
HORI, T ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4204-4208
[2]   CONVERSION OF ALLYLIC PHENYLSELENIDES TO THE REARRANGED ALLYLIC CHLORIDES BY N-CHLOROSUCCINIMIDE - MECHANISM OF SELENIUM-CATALYZED ALLYLIC CHLORINATION OF BETA-PINENE [J].
HORI, T ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4208-4210
[3]   SYNTHETIC APPLICATIONS OF ARYLSELENENIC AND ARYLSELENINIC ACIDS - CONVERSION OF OLEFINS TO ALLYLIC ALCOHOLS AND EPOXIDES [J].
HORI, T ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1689-1697
[4]   N-PHENYLSELENOPHTHALIMIDE (N-PSP) AND N-PHENYLSELENOSUCCINIMIDE (N-PSS) - 2 VERSATILE CARRIERS OF THE PHENYLSELENO GROUP- OXYSELENATION OF OLEFINS AND A SELENIUM-BASED MACROLIDE SYNTHESIS [J].
NICOLAOU, KC ;
CLAREMON, DA ;
BARNETTE, WE ;
SEITZ, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (13) :3704-3706
[5]  
PAULMIER C, 1984, SELENIUM REAGENTS IN
[6]   SYN ELIMINATION OF ALKYL SELENOXIDES - SIDE REACTIONS INVOLVING SELENENIC ACIDS - STRUCTURAL AND SOLVENT EFFECTS ON RATES [J].
REICH, HJ ;
WOLLOWITZ, S ;
TREND, JE ;
CHOW, F ;
WENDELBORN, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1697-1705
[7]   THE REACTION OF DIPHENYL DISELENIDE WITH PEROXYDISULFATE IONS IN METHANOL - A CONVENIENT PROCEDURE TO EFFECT THE METHOXYSELENENYLATION OF ALKENES [J].
TIECCO, M ;
TESTAFERRI, L ;
TINGOLI, M ;
CHIANELLI, D ;
BARTOLI, D .
TETRAHEDRON LETTERS, 1989, 30 (11) :1417-1420
[8]   THE USE OF SELENIUM CONTAINING INTERMEDIATES TO MEDIATE OR CATALYZE NEW ORGANIC-REACTIONS [J].
TIECCO, M ;
TINGOLI, M ;
TESTAFERRI, L .
PURE AND APPLIED CHEMISTRY, 1993, 65 (04) :715-722
[9]   RING-CLOSURE REACTIONS INITIATED BY THE PEROXYDISULFATE ION OXIDATION OF DIPHENYL DISELENIDE [J].
TIECCO, M ;
TESTAFERRI, L ;
TINGOLI, M ;
BARTOLI, D ;
BALDUCCI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :429-434
[10]   PHENYLSELENO-LACTONIZATION OF OLEFINIC NITRILES PROMOTED BY PEROXYDISULFATE ION OXIDATION OF DIPHENYL DISELENIDE [J].
TIECCO, M ;
TESTAFERRI, L ;
TINGOLI, M ;
BARTOLI, D .
TETRAHEDRON, 1989, 45 (21) :6819-6832