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Titolo:
Ring size effects in the C-2-C-6 biradical cyclisation of enyne-allenes and the relevance for neocarzinostatin
Autore:
Schmittel, M; Steffen, JP; Maywald, M; Engels, B; Helten, H; Musch, P;
Indirizzi:
Univ Gesamthsch Siegen, FB Chem Biol 8OC1, D-57068 Siegen, Germany Univ Gesamthsch Siegen Siegen Germany D-57068 1, D-57068 Siegen, Germany Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany Univ Wurzburg Wurzburg Germany D-97074 n Chem, D-97074 Wurzburg, Germany
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
fascicolo: 8, , anno: 2001,
pagine: 1331 - 1339
SICI:
1472-779X(2001):8<1331:RSEITC>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
MOLECULAR-ORBITAL METHODS; MYERS-SAITO REACTION; DNA STRAND CLEAVAGE; BASIS-SETS; CHROMOPHORE ANALOGS; DESIGNED MOLECULES; DIENEDIYNE CORE; ATOM-TRANSFER; CYCLIZATION; CHEMISTRY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
75
Recensione:
Indirizzi per estratti:
Indirizzo: Schmittel, M Univ Gesamthsch Siegen, FB Chem Biol 8OC1, Adolf Reichwein Str, D-57068 Siegen, Germany Univ Gesamthsch Siegen Adolf Reichwein Str Siegen Germany D-57068
Citazione:
M. Schmittel et al., "Ring size effects in the C-2-C-6 biradical cyclisation of enyne-allenes and the relevance for neocarzinostatin", J CHEM S P2, (8), 2001, pp. 1331-1339

Abstract

The regioselectivity of the thermal cyclisations of enyne-allenes 1 can betoggled as a function of the ring size of the cycloalkene. With a cyclopentene as the ene moiety the Myers-Saito (C-2-C-7) cycloaromatisation productis formed, whereas with six- and seven-membered cycloalkenes the novel C-2-C-6 cyclisation is observed. DFT calculations are used to rationalise these changes. The implications of these findings for alternative thermal biradical cyclisations of neocarzinostatin are discussed.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/04/20 alle ore 20:39:42