Dimethyl octamethyltricyclo[4.2.2.02,5]deca-3,7,9-triene-7,8-dicarboxylate (Cookson's diester) revisited: Cope rearrangement and epoxidation site selectivity

Autor:	I. G. Pitt, Richard A. Russell, Edward R. T. Tiekink, G. M. Elsey, Ronald N. Warrener
Rok vydání:	1994
Předmět:	chemistry.chemical_classification Structure analysis Diene Base (chemistry) Stereochemistry Site selectivity Organic Chemistry Biochemistry chemistry.chemical_compound chemistry Drug Discovery Stereoselectivity Selectivity Cope reaction Cope rearrangement
Zdroj:	Tetrahedron Letters. 35:1075-1078
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)79969-2
Popis:	Dimethyl octamethyltricyclo[4.2.2.0 2,5 ]deca-3,7,9-triene-7,8-dicarboxylate (Cookson's diester) ( 8 ) is rearranged thermally via a double Cope reaction to its ring-degenerate isomer ( 14 ). The structure of diester ( 8 ) (indirectly) and the rearrangement product ( 14 ) (directly) are placed on an unequivocal base by X-Ray structure analysis. AMI semi-empirical calculations support the preferential formation of ( 8 ) from the reaction of DMAD with transient intermediate diene ( 7 ). Epoxidation studies (mCPBA) have been conducted and firm site selectivities determined. A correction is made to an earlier report on the epoxidation selectivity of ( 18 ).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3dc8bed346beb23ee38f069091407c2f https://doi.org/10.1016/s0040-4039(00)79969-2 Zobrazit plný text záznamu