Synthesis and structural characterisation of the first example of a 3, 3′-diphospha-1,1′-biphospholyl ring system; crystal and molecular structure of P4C6But6

1993 ◽  
pp. 267-269 ◽  
Author(s):  
Salih S. Al-Juaid ◽  
Peter B. Hitchcock ◽  
Robson M. Matos ◽  
John F. Nixon
Keyword(s):  
Molecular Structure ◽  
Crystal And Molecular Structure ◽  
Ring System ◽  
Structural Characterisation

The crystal and molecular structure of 4-Bromo-1,1,3,3,5,7,7,9,9-nonamethylbicyclo[4,4,0]pentaborophane

1975 ◽  
Vol 28 (6) ◽  
pp. 1187 ◽  
Author(s):  
GR Clark ◽  
GJ Palenik
Keyword(s):  
Molecular Structure ◽  
Bond Length ◽  
Crystal And Molecular Structure ◽  
Bromine Atom ◽  
Chair Conformation ◽  
Ring System ◽  
Intensity Data ◽  
Internal Ring ◽  
Charge Delocalization ◽  
Cyclic System

Crystals of 4-bromo-1,1,3,3,5,7,7,9,9- nonamethylbicyclo[4,4,0]pentaborophane, C9H35B5P5Br, are monoclinic, with a = 9.502(3), b = 20.185(15), c = 13.604(4) Ǻ, β = 116.49(2)�. The space group is P21/c, with four molecules in the cell. Intensity data were collected by means of an automated diffractometer. The atomic positions have been determined by least-squares refinement of 2859 observed reflections. The final residual, R, is 0.077. The molecule contains a framework of alternat- ing boron and phosphorus atoms constituting a decalin-like ring system. The two cis-fused cyclo- hexane type rings are both in the chair conformation. The bromine atom is equatorially bonded to the boron atom in the 4-position. The Br-B bond length is 2.039(10) Ǻ. The average P-B and P-C distances are 1.943 and 1.828 Ǻ respectively. Average internal ring angles are 112.2� for P-B-P, and 113.6� for B-P-B. This geometry indicates only very slight charge delocalization in the cyclic system.

The Meisenheimer Rearrangement in Heterocyclic Synthesis. IV. Derivatives of the 2H,6H-1,5,4-Benzodioxazocine and 7H-1,6,5-Benzodioxazonine Ring Systems: X-Ray Crystal Structure of 10-Methoxy-5-methyl-7-phenyl-2,3,4,5-tetrahydro-7H-1,6,5-benzodioxazonine

1988 ◽  
Vol 41 (3) ◽  
pp. 293 ◽  
Author(s):  
JB Bremner ◽  
EJ Browne ◽  
LM Engelhardt ◽  
IWK Gunawardana ◽  
AH White
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Crystal And Molecular Structure ◽  
Ring System ◽  
Heterocyclic Synthesis ◽  
Rearrangement Product ◽  
Ring Systems ◽  
X Ray ◽  
Derivatives Of ◽  
Moderate Yield

Meisenheimer rearrangement of the N-oxides (4) derived from a series of 5-aryl-4-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepines (3) gave rise to eight derivatives (5) of the new 2H,6H-1,5,4-benzodioxazocine ring system. Reaction of 9-methoxy-5-methyl-6-phenyl-3,4,5,6- tetrahydro-2H-1,5-benzoxazocine (6) with 3-chloroperoxybenzoic acid gave an unstable N-oxide (7). A Meisenheimer rearrangement product from (7), 10-methoxy-5-methyl-7-phenyl-2,3,4,5-tetrahydro-7 H-1,6,5- benzodioxazonine (8), the first example of this ring system, was isolated directly in moderate yield on oxidation of (6) with cooling. The crystal and molecular structure of (8) has been determined by X-ray crystallographic methods.

Synthesis of 2,3-Dihydro-1,4,5-benzodioxazocines. X-ray structure of 6-Phenyl-2,3-dihydro-1,4,5-benzodioxazocine

1983 ◽  
Vol 36 (12) ◽  
pp. 2555 ◽  
Author(s):  
EJ Browne ◽  
LM Engelhardt ◽  
AH White
Keyword(s):  
Molecular Structure ◽  
Single Crystal ◽  
Crystal And Molecular Structure ◽  
Ring System ◽  
Cyclic Dimer ◽  
X Ray ◽  
Ray Methods ◽  
By Products

Derivatives (6a-c) of the 1,4,5-benzodioxazocine ring system have been prepared in low-to-moderate yields by hydrazinolysis of {2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxyethyloxy]aryl}phenylmethanones(5a-c), and cyclization of the products at pH c. 4. Only in the case of (6b) was a trace of a cyclic dimer (7b) detected, in contrast to the analogous preparations of the 2H-1,5,6-benzodioxazonine derivatives (1a-c) where 18-membered cyclic dimers (8a-c) formed as by-products. The crystal and molecular structure of 6-phenyl-2,3-dihydro-1,4-5-benzodioxazocine (6a) has been determined by single-crystal X-ray methods.

Synthesis of Some Thieno Analogs of the Protoberberine and Protopine Skeletons. X-Ray Crystal Structure of 9,10-Dimethoxy-5-methyl-4,5,6,7,12,13-hexahydrothieno[3,2-e][3]benzazeci n-12-one

1988 ◽  
Vol 41 (1) ◽  
pp. 111 ◽  
Author(s):  
JB Bremner ◽  
EJ Browne ◽  
LM Engelhardt ◽  
GS James ◽  
AH White
Keyword(s):  
Molecular Structure ◽  
Cyanogen Bromide ◽  
Methyl Ketone ◽  
Functional Group ◽  
Crystal And Molecular Structure ◽  
Major Product ◽  
Ring System ◽  
X Ray ◽  
A Minor ◽  
Ray Methods

The preparation of the tetracyclic derivatives, (5) and (11), thienanalogues of the tetrahydroprotoberberine alkaloids, is described. Cyanogen bromide-induced water solvolysis of these isomeric compounds proceeded by different routes. 9,10-Dimethoxy-4,7,12,12a- tetrahydro-5H-benzo[g] thieno [3,2-a] quinolizine (11) under these conditions gave as the major product 4-(2-hydroxymethyl-4,5- dimethoxybenzyl )-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5- carbonitrile (12); no azecino derivatives were detected. By contrast such cleavage of 2,3-dimethoxy-5,8,12,12a-tetrahydro-6H- benzo [a] thieno [3,2-g] quinolizine (5) gave a major solvolytic ring- expanded product, 12-hydroxy-9,10-dimethoxy-4,5,6,7,12,13- hexahydrothieno [3,2-e][3]benzazecine-5-carbonitrile (15), and a minor elimination product, (E)-9,10-dimethoxy-4,5,6,7-tetrahydrothieno[3,2- e][3]benzazecine-5-carbonitrile (16). These last two compounds are examples of a new tricyclic ring system. From functional group interconversions of (15) was derived the N- methyl ketone (18), the first thieno analogue of the protopine alkaloid system. The crystal and molecular structure of this compound, 9,10-dimethoxy-5-methyl-4,5,6,7,12,13-hexahydrothieno[3,2-e][3] benzazecin - 12-one (18), has been determined by single-crystal X-ray methods.

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