Unusual regio- and enantioselective [1,2]-Stevens rearrangement of a spirobi[dibenzazepinium] cation

Vial, Laurent; Gonçalves, Maria-Héléna; Morgantini, Pierre-Yves; Weber, Jacques; Bernardinelli, Gérald Hugues; Lacour, Jérôme

doi:10.1055/s-2004-829069

Scientific article

English

Unusual regio- and enantioselective [1,2]-Stevens rearrangement of a spirobi[dibenzazepinium] cation

ContributorsVial, Laurent; Gonçalves, Maria-Héléna; Morgantini, Pierre-Yves; Weber, Jacques; Bernardinelli, Gérald Hugues; Lacour, Jérôme

Published inSynlett, no. 9, p. 1565-1568

Publication date2004

Abstract

Highly symmetric spirobi[dibenzazepinium] cation 3 reacts with P4-t-Bu to form exclusively a ring-expanded tertiary amine; this unusual reactivity can be traced back to the geometry of the ylide.

Keywords

Ammonium
Rearrangements
Regioselectivity
Stereoselectivity
Ylides

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie physique

Research groups

Groupe Weber

Citation (ISO format)

VIAL, Laurent et al. Unusual regio- and enantioselective [1,2]-Stevens rearrangement of a spirobi[dibenzazepinium] cation. In: Synlett, 2004, n° 9, p. 1565–1568. doi: 10.1055/s-2004-829069

Identifiers

PID : unige:3256
DOI : 10.1055/s-2004-829069

Journal ISSN0936-5214

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Unusual regio- and enantioselective [1,2]-Stevens rearrangement of a spirobi[dibenzazepinium] cation

Highly symmetric spirobi[dibenzazepinium] cation 3 reacts with P4-t-Bu to form exclusively a ring-expanded tertiary amine; this unusual reactivity can be traced back to the geometry of the ylide.

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