The synthesis and x‐ray structure of endo‐7‐chloro‐7‐phenyl‐2,5‐dioxabicyclo[4.1.0]heptane

Oliver, J. D.; Woodyard, James D.; Rush, Peder E.; Curtis, John R.

doi:10.1002/jhet.5570110657

Cited by 9 publications

(1 citation statement)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The title compound, hereinafter referred to as DOBH, has been isolated as the single product of the reaction between benzal chloride, potassium t-butoxide and 1,4-diox-2-ene (Oliver, Woodyard, Rush & Curtis, 1974); however physical and analytical data did not allow unambiguous assignment of the stereochemistry for the compound. An interest in molecules containing a highly strained ring fused to a formerly strain-free ring resulted in our focusing attention on this compound.…”

Section: Introductionmentioning

confidence: 99%

The crystal and molecular structure of exo-7-chloro-7-phenyl-2,5-dioxabicyclo[4.1.0]heptane

Oliver¹,

Henslee²,

Rush³

1976

Acta Crystallogr Sect B

View full text Add to dashboard Cite

The structure of exo-7-chloro-7-phenyl-2,5-dioxabicyclo[4,1,O]heptane has been determined by singlecrystal X-ray diffraction methods. The crystals are monoclinic, P21/n with a= 5"840 (1), b= 16.039 (1), c= 10"692 (1)A, fl=90"919 (6) ° and Z=4. Intensity data were collected on a manually operated diffractometer using Cu K~ radiation. The structure was solved by direct methods and has been refined by block-diagonal least-squares techniques to R = 0"068 (weighted R = 0"056) including all the hydrogen atoms. The geometry of the cyclopropyl ring is normal. The dioxanyl ring has adopted an envelope conformation in which three of the C-O distances are significantly shortened. This unusual geometry of the six-membered ring is the consequence of the strain introduced by fusion of the three-membered and six-membered rings.

show abstract

Section: Introductionmentioning

confidence: 99%