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Titolo:
THEXYLHALOBORANE-METHYL SULFIDE AS HYDROBORATING AND STEREOSELECTIVE REDUCING AGENT
Autore:
CHA JS; MIN SJ; KIM JM;
Indirizzi:
YEUNGNAM UNIV,DEPT CHEM KYONGSAN 712749 SOUTH KOREA
Titolo Testata:
Bulletin of the Korean Chemical Society
fascicolo: 6, volume: 15, anno: 1994,
pagine: 478 - 483
SICI:
0253-2964(1994)15:6<478:TSAHAS>2.0.ZU;2-E
Fonte:
ISI
Lingua:
ENG
Soggetto:
THEXYLBROMOBORANE-DIMETHYL SULFIDE; REPRESENTATIVE FUNCTIONAL-GROUPS; UNSATURATED CARBOXYLIC-ACIDS; FACILE REDUCTION; SELECTIVE REDUCTIONS; ORGANIC-COMPOUNDS; METAL-HYDRIDES; THEXYLCHLOROBORANE; ALDEHYDES; 9-BORABICYCLO)3.3.1>NONANE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
33
Recensione:
Indirizzi per estratti:
Citazione:
J.S. Cha et al., "THEXYLHALOBORANE-METHYL SULFIDE AS HYDROBORATING AND STEREOSELECTIVE REDUCING AGENT", Bulletin of the Korean Chemical Society, 15(6), 1994, pp. 478-483

Abstract

Reactions of alkenes and alkynes with thexylhaloborane-methyl sulfide(ThxBHX . SMe2, X= Cl, Br, I) were investigated in detail in order toelucidate the effect of halogen substituent in thexylborane and henceestablish their usefulness as hydroborating agent. The reagents readily hydroborated alkenes at 50-degrees-C and alkynes at 25-degrees-C inexceptional regioselectivity. Especially, the selectivity achieved bythe bromo and iodo derivative reaches essentially 100%. In addition to that, ThxBHX.SMe2 was applied to the reduction of cyclic ketones to examine its stereoselectivity. The halogen substituent in thexylboraneplays an important role in the stereoselective reduction. The stereoselectivity increased dramatically with increasing steric size of the substituent. Finally, the iodo derivative achieved highly stereoselective reduction, such selectivity being comparable to that previously achieved with trialkylborohydrides.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/11/20 alle ore 06:54:41