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Titolo:
FACE SELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF BENZONITRILE OXIDE WITH 5-SUBSTITUTED ADAMANTANE-2-THIONES AND 2-METHYLENEADAMANTANES
Autore:
CHUNG WS; TSAI TL; HO CC; CHIANG MYN; LENOBLE WJ;
Indirizzi:
NATL CHIAO TUNG UNIV,DEPT APPL CHEM HSINCHU 30050 TAIWAN NATL SUN YAT SEN UNIV,DEPT CHEM KAOHSIUNG 804 TAIWAN SUNY STONY BROOK,DEPT CHEM STONY BROOK NY 11794
Titolo Testata:
Journal of organic chemistry
fascicolo: 14, volume: 62, anno: 1997,
pagine: 4672 - 4676
SICI:
0022-3263(1997)62:14<4672:FSIT1C>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
THIOCARBONYL COMPOUNDS; THERMAL CYCLOADDITION; CYCLO-ADDITION; ADAMANTANETHIONE; ADAMANTANONES; CAPTURE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
27
Recensione:
Indirizzi per estratti:
Citazione:
W.S. Chung et al., "FACE SELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF BENZONITRILE OXIDE WITH 5-SUBSTITUTED ADAMANTANE-2-THIONES AND 2-METHYLENEADAMANTANES", Journal of organic chemistry, 62(14), 1997, pp. 4672-4676

Abstract

The 1,3-dipolar cycloaddition reactions of benzonitrile oxide with 5-substituted adamantane-2-thiones (2-X) and 2-methyleneadamantanes (3-X) produced two geometrically isomeric Delta(2)-1,4,2-oxathiazolines (5-Xs) and two Delta(2)-isoxazolines (6-Xs), respectively. The substituent was varied from fluoro, chloro, bromo, to phenyl. X-ray single-crystal analysis confirmed the configuration of (Z)-5-F. The produce formation bias resulting from the favored attack of nitrile oxide on the zu-face is discussed in terms of transition-state hyperconjugation and frontier molecular orbital theory.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 13/07/20 alle ore 14:37:54