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Acta Crystallographica Section E-structure Reports Online | 2008

Dimethyl 6H,12H-5,11-methano­dibenzo[b,f][1,5]diazo­cine-2,8-diacetate

Masoud Faroughi; Paul R. Jensen; Andrew C. Try

The asymmetric unit of the title compound, C21H22N2O4, a Tröger’s base analogue derived from methyl 4-aminophenylacetate, contains two crystallographically independent molecules with dihedral angles of 88.44 (5) and 88.68 (6)° between the two benzene rings.


Acta Crystallographica Section E-structure Reports Online | 2008

6H,12H-5,11-Ethano­dibenzo[b,f][1,5]diazo­cine

Masoud Faroughi; Andrew C. Try; Peter Turner

In the molecule of the title compound, C16H16N2, the ethano-strapped analogue of unsubstituted Tröger’s base, the dihedral angle between the two benzene rings is 75.85 (4)°, the smallest angle measured for an ethano-strapped analogue.


Acta Crystallographica Section E: Crystallographic Communications | 2007

6H,12H-5, 11-Methanodibenzo[b,f][1,5]diazocine

Masoud Faroughi; Paul R. Jensen; Andrew C. Try

Methods for facile synthesis of symmetric and unsymmetric functionalized analogues of Trögers base were developed with use of 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (2) as the starting material. C(2)-symmetric 2,8-disubstituted analogues of Trögers base (4a-f) were synthesized via double bromine-lithium exchange of 2 followed by quench with electrophiles. Desymmetrization via single bromine-lithium exchange of 2, followed by quench with electrophiles, afforded asymmetric analogues of Trögers base (6a-g). Further reaction of 2-bromo-8-(trimethylsilyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (6b) produced 7a-c via single bromine-lithium exchange and subsequent quench with electrophiles.


Acta Crystallographica Section E-structure Reports Online | 2007

2,8-Dichloro-6H,12H-5,11-ethano-dibenzo[b,f][1,5]diazo-cine.

Masoud Faroughi; Andrew C. Try; Peter Turner

In the molecule of the title compound, C16H14Cl2N2, the ethano-strapped 2,8-dichloro analogue of Tröger’s base, the dihedral angle between the two benzene rings is 87.01 (3)°.


Tetrahedron Letters | 2007

Changing the shape of Tröger’s base

Masoud Faroughi; Andrew C. Try; John A. Klepetko; Peter Turner


European Journal of Organic Chemistry | 2009

One-Step Synthesis of Tröger's Base Hybrids Containing at Least One Halogen Atom

Masoud Faroughi; Kai-Xian Zhu; Paul R. Jensen; Donald C. Craig; Andrew C. Try


Acta Crystallographica Section E: Crystallographic Communications | 2006

2,4,8,10-Tetra­bromo-6H,12H-5,11-methano­dibenzo[b,f][1,5]diazo­cine

Masoud Faroughi; Andrew C. Try; Peter Turner


Arkivoc | 2009

Halogenation of Tröger’s base analogues

Masoud Faroughi; Paul R. Jensen; Andrew C. Try


Acta Crystallographica Section E-structure Reports Online | 2006

2,8-Dibromo-6H, 12H-5,11-methanodibenzo[b,f][1,5]diazocine

Masoud Faroughi; Andrew C. Try; Peter Turner


Acta Crystallographica Section E-structure Reports Online | 2007

2,8-Dichloro-6 H ,12 H -5,11-methanodibenzo[ b , f ][1,5]diazocine

Masoud Faroughi; Andrew C. Try; Peter J. Turner

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