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Titolo:
Synthesis and physical properties of sterically congested cycloalkenes, 1,2-di-tert-butyl-3,3,5,5-tetramethylcyclopentene and 1,2-di-tert-butyl-3,3,6,6-tetramethylcyclohexene
Autore:
Ishii, A; Tsuchiya, C; Shimada, T; Furusawa, K; Omata, T; Nakayama, J;
Indirizzi:
Saitama Univ, Fac Sci, Dept Chem, Urawa, Saitama 3388570, Japan Saitama Univ Urawa Saitama Japan 3388570 m, Urawa, Saitama 3388570, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 6, volume: 65, anno: 2000,
pagine: 1799 - 1806
SICI:
0022-3263(20000324)65:6<1799:SAPPOS>2.0.ZU;2-V
Fonte:
ISI
Lingua:
ENG
Soggetto:
TETRA-TERT-BUTYLETHYLENE; LOW-VALENT TITANIUM; HINDERED ALKENES; S-OXIDES; X-RAY; DERIVATIVES; 1,3-DITHIETANE; SELENOKETONES; THIOKETONES; CHEMISTRY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
55
Recensione:
Indirizzi per estratti:
Indirizzo: Ishii, A Saitama Univ, Fac Sci, Dept Chem, Urawa, Saitama 3388570, Japan Saitama Univ Urawa Saitama Japan 3388570 Saitama 3388570, Japan
Citazione:
A. Ishii et al., "Synthesis and physical properties of sterically congested cycloalkenes, 1,2-di-tert-butyl-3,3,5,5-tetramethylcyclopentene and 1,2-di-tert-butyl-3,3,6,6-tetramethylcyclohexene", J ORG CHEM, 65(6), 2000, pp. 1799-1806

Abstract

Two sterically congested cycloalkenes (9 and 10), congeners of tetra-tert-butylethylene, were synthesized and characterized. Oxidation of the bicyclic 1,3-dithietane 8 with dimethyldioxirane (DMD) gave the endo,endo-disulfoxide 13, thermal isomerization of which to the endo,exo-disulfoxide 15 followed by oxidation with DMD gave the trioxide 18. Heating 18 in refluxing 1,3-dimethyl-2-imidazolidinone furnished 1,2-di-tert-butyl-3,3,5,5-tetramethylcyclopentene (9) in 69% yield by a 2-fold extrusion process. The reaction of the I,g-diketone dihydrazone 23 with Se2Cl2 gave the selenadiazoline 34 and the 1,3-diselenetane 35. Heating 34 at 115-130 degrees C gave 1,2-di-tert-butyl-3,3,6,6-tetramethylcyclohexene (10), a "didehydro" derivative of tetra-tert-butylethylene, in 43% yield. The C=C bond in 10 is strained in degree comparable to those of most strained alkenes reported so far.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 31/03/20 alle ore 05:04:21