The crystal and molecular structure of <i>anti</i>-7-norbornenyl <i>p</i>-bromobenzoate

Macdonald, Alexander; Trotter, James

doi:10.1107/s0365110x65003596

Cited by 35 publications

(10 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1. The conformation of the norbornene nucleus is in essential agreement with the results of previous crystallographic work, such as the structure of anti-7-norbornenyl p-bromobenzoate (Macdonald & Trotter, 1965b), where most of the bond lengths and angles are nearly identical with ours. A useful comparison can be made also with the tricyclo[3,2,1,02 4]octane nucleus (Macdonald & Trotter, 1965a) and especially with cyclopentadiene dimer (Destro, Gramaccioli & Simonetta, 1968;Bellobono, Destro, Graccioli & Simonetta, * The correction for bond angles was made under the assumption that triangulation is valid for deducing intramolecular angles from corrected distances when dealing with a rigid body.…”

Section: The Molecular Structuresupporting

confidence: 90%

The structure of 5-norbornene-2,3-endo-dicarboxylic anhydride

Destro¹,

Filippini²,

Gramaccioli³

et al. 1969

Acta Crystallogr Sect B

View full text Add to dashboard Cite

Acta Cryst. (1969). B25, 2465The Structure of 5-Norbornene-2,3-endo-diearboxylie Anhydride BY RICCARDO DESTRO, GIUSEPPE FILIPPINI, CARLO MARIA GRAMACCIOLI AND MASSIMO SIMONETTA Istituto di Chimica Fisica, Universitdt di Milano, Milano, Italy (Received 3 February 1969)The crystal and molecular structure of 5-norbornene-2,3-endo-dicarboxylic anhydride* has been determined and refined by least-squares methods. The crystals are orthorhombic, space group P2~212j, with a= 13"539, b=9"565, c=5"972/~ and four molecules per unit cell. Intensity data were collected visually from Weissenberg photographs about two crystal axes. The final R index is 0.071 ; the average standard deviation in the atomic positions is about 0.004 A,. The anisotropic temperature factors of the heavier atoms in the molecule can be accounted for by a Schomaker-Trueblood rigid-body treatment; on this basis, corrections to the observed bond distances are in the range 0"007-0.010/~. In the norbornene nucleus, the bridgehead angle C(1)-C(7)-C(4) is 93.5 °. The geometry of the anhydride group is closely similar to that found in succinic anhydride. The two C-C single bonds which connect the anhydride ring with the cyclopentene ring are found to be significantly longer (1.57 and 1.58/~) than normal. A similar feature observed in cyclopentadiene dimer probably accounts for its chemical reactivity in the Cope rearrangement.

show abstract

Section: The Molecular Structuresupporting

confidence: 90%

The structure of 5-norbornene-2,3-endo-dicarboxylic anhydride

Destro¹,

Filippini²,

Gramaccioli³

et al. 1969

Acta Crystallogr Sect B

View full text Add to dashboard Cite

show abstract

“…Tables of observed and calculated structure factors are available from the Depository of Unpublished Data.' ~o s t bond lengths and angles in the hydrocarbon moiety agree well with values found for various uncomplexed bicyclo[2,2,l]hept-2-ene derivatives (11)(12)(13)(14). Bond lengths are not significantly different (G3a) from standard values (15) and like the other X-ray structure determinations of such molecules (1 1-14), the bonds C(1)-C(7) (1.53 l(5) A) and C(4)-C(7) (1.531 (5) Csp3-Csp2, average = 1.522(6) A do not differ significantly from these values.…”

supporting

confidence: 80%

Chemistry of proximal π-bond systems. Part IV. The structure of 5,6-dimethylenebicyclo[2,2,1]hept-2-ene molybdenum tricarbonyl

Anderson¹,

Robertson²,

Butler³

1976

Can. J. Chem.

View full text Add to dashboard Cite

Crystals of 5,6-dimethylenebicyclo[2,2,1]hept-2-ene molybdenum tricarbonyl 1 (M = Mo) are monoclinic, a = 7.4451(3) Å, b = 13.5783(7) Å, c = 11.2691(4) Å, β = 92.593(3)°, Z = 4, space group P21/c. The structure was solved by the 'heavy atom' method and was refined by full-matrix least square procedures to a final R = 0.031. The weighted R factor was 0.051. Experimental bond lengths and angles are close to other reported values for bicyclo[2,2,1]hept-2-ene systems except for three major distortions in the triene ligand namely: the closing of the angles C(2)—C(1)—C(6) and C(3)—C(4)—C(5) by about 5.3°, the bending of the butadiene fragment plane C(8)—C(5)—C(6)—C(9) toward the metal atom by about 20° and the twisting of the terminal methylene hydrogens H(8i) and H(9i) out of the butadiene fragment plane (0.44 and 0.53 Å respectively) away from the molybdenum atom.

show abstract

“…Weighted least-squares mean planes are given i n Table 8. The structural parameters of (9) are compared with those of related compounds (13)(14)(15)(16)(17)(18)(19)(20) and oximes (21)(22)(23)(24)(25)(26)(27)(28)(29) in Table 9. Important inter-and intramolecular nonbonded contacts and details of the hydrogen bonding scheme are given in Table 10.…”

Section: Resultsmentioning

confidence: 99%

“…This involves cyclization of the en01 acetate (2) of dihydrocarvone (1) and the logical extension of this approach in the sesquiterpene area prompted synthesis of the en01 acetate (5) of dihydrocryptomerion (4) and subjection of this to the same cyclization conditions. In this way it was hoped to achieve a simple synthesis of campherenone (6) which occupied a key position in the general synthetic strategy (16). In the event, cyclization of the en01 acetate (5) with boron trifluoride in wet methylene chloride provided a mixture of products from which the main components (A, B, and C) could be isolated by column chromatography (silica) and preparative g.1.c.…”

Section: Introductionmentioning

confidence: 99%

Crystal and Molecular Structure of (±)-7,7-(2′,2′-Dimethyl)pentamethylene-1-methyl-norbornane-2-oxime

Rettig¹,

Trotter²

1975

Can. J. Chem.

View full text Add to dashboard Cite

Crystals of (±)-7,7-(2′,2′-dimethyl)pentamethylene-1-methyl-norbornane-2-oxime are monoclinic, a = 9.202(2), b = 12.852(3), c = 12.698(3) Å, β = 110.83(2)°, Z = 4, space group P21/c. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to a final R of 0.048 for 1538 reflections with I ≥ 3σ(I). The crystal structure consists of pairs of molecules linked by N … H—O hydrogen bonds (N … O = 2.821(3) Å ) to form centrosymmetric dimers. Bond distances are as follows: C—N = 1.266(3), N—O = 1.426(3), mean C(sp3)—C(sp3) = 1.540, and mean C(sp3)—C(sp3) = 1.511 Å.

show abstract

The crystal and molecular structure of anti-7-norbornenyl p-bromobenzoate

Cited by 35 publications

References 1 publication

The structure of 5-norbornene-2,3-endo-dicarboxylic anhydride

The structure of 5-norbornene-2,3-endo-dicarboxylic anhydride

Chemistry of proximal π-bond systems. Part IV. The structure of 5,6-dimethylenebicyclo[2,2,1]hept-2-ene molybdenum tricarbonyl

Crystal and Molecular Structure of (±)-7,7-(2′,2′-Dimethyl)pentamethylene-1-methyl-norbornane-2-oxime

Contact Info

Product

Resources

About