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Titolo:
Inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones with enol ethers and styrene
Autore:
Gao, SY; Ko, S; Lin, YL; Peddinti, RK; Liao, CC;
Indirizzi:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan Natl Tsing Hua UnivHsinchu Taiwan 30013 ept Chem, Hsinchu 30013, Taiwan
Titolo Testata:
TETRAHEDRON
fascicolo: 2, volume: 57, anno: 2001,
pagine: 297 - 308
SICI:
0040-4020(20010107)57:2<297:IDROMO>2.0.ZU;2-0
Fonte:
ISI
Lingua:
ENG
Soggetto:
STEREOSELECTIVE SYNTHESIS; METHYL VANILLATE; 2-METHOXYPHENOLS; DERIVATIVES; BICYCLO<2.2.2>OCTENONES; DIENOPHILES; CHEMISTRY; SYSTEM;
Keywords:
orthoquinone monoketal; 2-methoxyphenols; diacetoxyiodobenzene; bicyclo[2.2.2]octenones; inverse-electron-demand Diels-Alder reaction;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
51
Recensione:
Indirizzi per estratti:
Indirizzo: Liao, CC Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan Natl Tsing Hua Univ Hsinchu Taiwan 30013 Hsinchu 30013, Taiwan
Citazione:
S.Y. Gao et al., "Inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones with enol ethers and styrene", TETRAHEDRON, 57(2), 2001, pp. 297-308

Abstract

Regio- and stereoslective inverse-electron-demand Diels-Alder reactions ofmasked o-benzoquinones (MOBs) la-lh derived from the corresponding 2-methoxyphenols 2a-2h with benzyl vinyl ether, dihydrofuran and styrene to affordthe highly functionalized bicyclo[2.2.2]octenone derivatives are described. The MOBs having electron-deficient substituents were found to undergo more facile Diels-Alder cycloadditions with these dienophiles. The electron-rich dienophile dihydropyran is not a suitable 2 pi -partner for MOBs. Attempts are made to explain the observed regiochemistry of these Diels-Alder cycloadditions in terms of frontier molecular orbital theory. (C) 2000 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/09/20 alle ore 08:10:17