5032-03-1Relevant articles and documents
Selective sp3 C-H bond activation based on a carbocation relay: Friedel-Crafts reaction with alkanes as the alkylating component
Wang, Jie,Zhou, Pengfei,Wang, Yang
experimental part, p. 264 - 270 (2011/03/20)
A highly efficient and selective intramolecular Friedel-Crafts reaction of 3-methylbutyl or 4-methylpentyl-substituted aromatics has been developed using a carbocation relay strategy through selective sp3 C-H bond activation, providing a facile and cost-effective approach for the construction of benzocyclic compounds. A variety of 1,1-dimethylindane and naphthalene derivatives have been prepared from very simple starting materials in good yields with high selectivity. The present strategy has provided a new example of a Friedel-Crafts reaction with alkanes as the alkylating component and constitutes a convenient approach to selective C-H bond activation and functionalization of alkane derivatives. A highly efficient and selective intramolecular Friedel-Crafts reaction of 3-methylbutyl or 4-methylpentyl- substituted aromatics has been developed using a carbocation relay strategy through selective sp3 C-H bond activation. The approach provides a facile and cost-effective route to benzocyclic compounds. Copyright
Conformational analysis of 3-substituted-2,3,4,5-tetrahydro-1-benzoxepin by 1H and 13C nuclear magnetic resonance
Lachapelle, A.,St-Jacques, M.
, p. 2575 - 2594 (2007/10/02)
2,3,4,5-Tetrahydro-1-benzoxepin (8) and its 3-substituted derivatives (9-13) have been studied by 1H and 13C dynamic nuclear magnetic resonance in a few solvent systems.The results show that, while 8 and its methyl derivative 9 exist solely in chair forms (C for 8 and Ce:Ca (96:4) for 9), the twist-boat (TB) conformation contributes significantly to the conformational equilibra of the derivatives 3-methoxy 10 (Ca:Ce:TB, 70:20:10), 3,3-dimethyl 11 (C:TB, 90:10), 3,3-methylmethoxy 12 (Ca:Ce:TB, 89:4:7), and 3,3-dimethoxy 13 (C:TB, 92:8).The analysis of several factors (steric, electrostatic, and electronic) on the conformational behaviour of these molecules shows why the TB form is a viable conformational alternative to destabilized chair forms in this benzoxepin system.