The crystal and molecular structure of 12-methyl-11,13-dioxo-12-azapentacyclo[4,4,3,01.6,02.10,05.7]trideca-3,8-diene

Hwang, Kwang Jin; Donohue, Jerry; Tsai, Chun Che

doi:10.1107/s0567740872004935

Cited by 6 publications

(1 citation statement)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pasternak (1951) found the ethylenic C-C bond in pentachlorocyclohexene to be 1.22 A, but the C atoms in that study could, of course, be located only with very low precision. In a different cyclohexene derivative Hwang, Donohue & Tsai (1972) found an ethylenic bond of length 1.304 (7) A, similar to the values of 1.316 (7) and 1.319 (7) A found here. All of these are shorter than the value of 1-335 (5) A~ in various ethylenes (Sutton, 1965).…”

Section: ~)supporting

confidence: 75%

trans-4a-Acetoxy-8a-chloro-1,4,4a,5,8,8a-hexahydronaphthalene

Boggs¹,

Donohue²

1976

Acta Crystallogr Sect B

Self Cite

View full text Add to dashboard Cite

Abstract. Crystals of C1202H15C1 are orthorhombic, with a= 11.006 (5), b= 14.190 (9), e=7.359 (3) A, space group P212121, Z--4, De= 1.22 g cm -3. Full-matrix least-squares refinement gave a final R of 4.4 %. C-CI is 1.823 (4) A, a value surprisingly long in view of the unreactivity of this tertiary chloride with hot alcoholic silver nitrate. Other structural features are typical.Introduction. Starting with naphthalene Roberts (1971), using the reaction sequence of HCI addition to the 4a,8a-epoxide of isotetralin and acetylation, prepared what was presumed to be the title compound (1).

show abstract

Section: ~)supporting

confidence: 75%

trans-4a-Acetoxy-8a-chloro-1,4,4a,5,8,8a-hexahydronaphthalene

Boggs¹,

Donohue²

1976

Acta Crystallogr Sect B

Self Cite

View full text Add to dashboard Cite

show abstract

Ein planarer Cyclohexan‐Ring: Röntgen‐Strukturanalyse von 9‐Cyan‐anti‐dioxa‐tris‐σ‐homobenzol

et al. 1973

View full text Add to dashboard Cite

A Planar Cyclohexane Ring: X‐Ray Analysis of 9‐Cyano‐anti‐dioxatris‐σ‐homobenzene

Kabuto¹,

Yagihara²,

Asao³

et al. 1973

Angew. Chem. Int. Ed. Engl.

View full text Add to dashboard Cite

Recently a general synthetic route to trishomobenzene has been established,and some interesting properties which may arise from the strained character of the molecule reported"]. Particular interest attaches to changes in geometry of the central cyclohexane ring when annelated to three strained small rings. We have established the structure of the molecule by X-ray analysis of 9-cyano-3,6-dioxatetracyclo[6.1 .0.O2.'.Os.']nonane ( 1 )['I. As far as we know, this is the first structural report on the tris-o-homobenzene system.( 1) H HCompound ( I ) crystallizes in the monocyclic space group P2,/c with a=6.501, b= 13.215, c=8.795A; p = 115.74'; Z = 4 : D r x p = 1.45g/cm3, D,,,,= 1.46g/cm3. A single crystal (0.2 x 0.2 x 0.25 mm) was examined with Rigaku automatically controlled four circle X-ray diffractometer; a total of 1289 reflections (within 28=55 ) were measured using M O K~ radiation. The structure was solved by a direct method and the parameters were refined by a block-diagonal least-squares method. After several refinements, all the hydrogen atoms were found from a difference Fourier synthesis. Further anisotropic least-squares refinement (C, 0, N) and simultaneous isotropic least-squares refinement (H) gave an R-factor of 0.048.The most important geometrical data are shown in Figure 1. As expected, the cyclohexane ring of ( I ) has a planar conformation: the maximum deviation from the plane through C' to C6 is only 0.008A. The dihedral angle between this plane and the cyclopropane ring (75.8") is similar to those in anti-bromobishomoquinone (75-77')r3] and 2,5-dimethyl-7,7-dicyanonorcaradiene (73")C4]. The oxirane rings inclined in the opposite direction exhibit comparable dihedral angles (75.2" for C3C401 and 74.9' for C5C60').The influence of the "unsaturated character" of the threemembered ring on the bond length warrants atteation: The C'-Ch, C2-C3, and C4-C5 bonds (av. 1.480A) ade significantly shorter than sp3-sp3 single bonds (1.54 A), and close to sp'-spz single bonds (1.48 A). This would indicate that multi-conjugated interactions occur between three-membered rings, as assumed between cyclopropane rings and double bondst3-'I.A planar six-membered ring results in expansion of the "intracyclic" bond angles (120,), thus leading to a tilting Several years ago we reported the preparation of (diethylcarbamoy1)lithiurn ( 2 b ) by cleavage of bis(diethy1carba-moy1)mercury ( 3 ) with butyllithium['. '1. With carbonyl compounds, (2 h ) affords, after hydrolysis, a-hydroxy N,Ndiethylcarboxyamides and is thus a reagent that makes it possible to introduce the carbamoyl group into carbonyl compounds[', 31. The preparation of ( 3 ) is, however, rather troublesome[41 and not without danger, so we sought a simpler access to reagents of type (?)L51.

show abstract

The crystal and molecular structure of 12-methyl-11,13-dioxo-12-azapentacyclo[4,4,3,01.6,02.10,05.7]trideca-3,8-diene

Cited by 6 publications

References 5 publications

trans-4a-Acetoxy-8a-chloro-1,4,4a,5,8,8a-hexahydronaphthalene

trans-4a-Acetoxy-8a-chloro-1,4,4a,5,8,8a-hexahydronaphthalene

Ein planarer Cyclohexan‐Ring: Röntgen‐Strukturanalyse von 9‐Cyan‐anti‐dioxa‐tris‐σ‐homobenzol

A Planar Cyclohexane Ring: X‐Ray Analysis of 9‐Cyano‐anti‐dioxatris‐σ‐homobenzene

Contact Info

Product

Resources

About