The structure of PO-substituted norcaradienes. II. The crystal and molecular structures of dimethyl 2,5-dichloro-7-phenylnorcaradiene-7-phosphonate and dimethyl 2,5-dibromo-7-phenylnorcaradiene-7-phosphonate

Maas, Gerhard; Fischer, K.; Regitz, Manfred

doi:10.1107/s0567740874008302

Cited by 8 publications

(1 citation statement)

References 9 publications

(13 reference statements)

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“…The two bonds adjacent to the cyclopropyl ring are slightly shorter than their normal values in non-fused ring systems. A similar behavior has been observed in DOBH and in norcaradiene structures (Fritchie, 1966;Maas, Fischer & Regitz, 1974).…”

Section: C12supporting

confidence: 48%

endo-7-Chloro-7-phenyl-2-oxabicyclo[4.1.0]heptane

Henslee¹,

Woodyard²,

Oliver³

1976

Acta Crystallogr Sect B

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Abstract. C12H13OC1, F.W. 208-7; monoclinic, P21/c; a= 11.929 (1), b=7.469 (1), c= 11.900 (2) A, fl=96.25 (1) °; Dx= 1.315 g cm-3 for Z=4, Do= 1.317 g cm-3; V= 1054 A3;/t=28.9 cm -1. The structure was solved by the heavy-atom method and refined to R=0.074.The tetrahydropyran ring is in an envelope conformation with only one atom being significantly out of the plane defined by the other five non-hydrogen atoms of that moiety. The phenyl ring is oriented parallel to the bridgehead bond of the bicyclic system. endo-7-CHLORO-7-PHENYL-2-OXABICYCLO[4,1,0]HEPTANE

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Section: C12supporting

confidence: 48%

endo-7-Chloro-7-phenyl-2-oxabicyclo[4.1.0]heptane

Henslee¹,

Woodyard²,

Oliver³

1976

Acta Crystallogr Sect B

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Chemie der Phosphorylcarbene

Regitz

1975

Angewandte Chemie

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Phosphorylcarbene sind erst in den letzten Jahren bei synthetischen Versuchen auf dem Gebiet der Phosphoryldiazoalkane bekannt geworden. Ihr praparativer Wert besteht zum einen in der Einfiihrung von Phosphorylgruppen in organische Verbindungen, etwa bei der Phosphorylcyclopropanierung von Alkenen oder Arenen und der Phosphorylcyclopropenierung von Alkinen; zum anderen gehen die Phosphorylcarbene leicht Umlagerungen ein: Hydrid-, Alkyl-, Aryl-und Acylverschiebungen fuhren zu phosphorylierten Alkenen. Die Phosphorylcarben/Methylenphosphanoxid-Umlagerung macht die kurzlebigen P-Analoga der Ketene zuganglich. Die Vinylcarben/Allen-Umlagerung schlierjlich wurde erst in diesem Zusammenhang entdeckt: sie konkurriert mit dem RingschluR zum Cyclopropen.

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Chemistry of Phosphorylcarbenes

Regits

1975

Angew. Chem. Int. Ed. Engl.

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Phosphorylcarbenes, which have become known only recently during synthetic experiments in the field of phosphoryldiazoalkanes, have twofold preparative value. In the first place, they can be used to introduce phosphoryl groups into organic compounds, as in the phosphoryl‐cyclopropanation of alkenes or arenes and in the phosphorylcyclopropenation of alkynes. Secondly, phosphorylcarbenes readily undergo rearrangements; hydride, alkyl, aryl, or acyl shifts lead to phosphorylated alkenes. The phosphorylcarbene/methylenephosphane oxide rearrangement provides access to the short‐lived P analogs of the ketenes. Finally, the vinylcarbene/allene rearrangement was first discovered in this connection; it competes with ring closure to the cyclopropene.

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The structure of PO-substituted norcaradienes. II. The crystal and molecular structures of dimethyl 2,5-dichloro-7-phenylnorcaradiene-7-phosphonate and dimethyl 2,5-dibromo-7-phenylnorcaradiene-7-phosphonate

Cited by 8 publications

References 9 publications

endo-7-Chloro-7-phenyl-2-oxabicyclo[4.1.0]heptane

endo-7-Chloro-7-phenyl-2-oxabicyclo[4.1.0]heptane

Chemie der Phosphorylcarbene

Chemistry of Phosphorylcarbenes

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