The stereochemical course of the generation and interception of a six-membered cyclic allene: 3 delta(2)-1H-naphthalene (2,3-didehydro-1,2-dihydronaphthalene)

• Published in: European journal of organic chemistry Vol. 2006; no. 22; pp. 5045 - 5058
• Main Authors: Christl, Manfred, Braun, Martin, Fischer, Hartmut, Groetsch, Stefan, Mueller, Germar, Leusser, Dirk, Deuerlein, Stephan, Stalke, Dietmar, Arnone, Mario, Engels, Bernd
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 13.11.2006
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; enantioselectivity; APPROXIMATION; CONVERSION; cycloadditions; quantum chemistry calculations; COMPUTATIONAL ASSESSMENT; ELECTRONIC-STRUCTURES; ATOMS LI; CYCLOALLENES; 1,2,4-CYCLOHEXATRIENE; cyclic allenes; CD spectra; CHIRALITY; DERIVATIVES; GAUSSIAN-BASIS SETS

The bromofluorocarbene adduct rac-1 of indene, possessing the fluorine atom at the endo position, is a useful substrate for the generation of the isonaphthalene 4 by the Doering-Moore-Skattebol reaction. By resolution of rac-1, an enantiomerically pure precursor of a six-membered cyclic allene was o...