ChemInform Abstract: INTRAMOLEKULARE REAKTIONEN VON VINYL‐ UND ALLY‐PHOSPHORYL‐CARBENEN

Hartmann, A.; Welter, W.; Regitz, Manfred

doi:10.1002/chin.197432365

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Intermolecular Reactions[*'1

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1975

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“…221. At the same time, as an indication of its triplet character, (32) abstracts hydrogen from the cyclohexene with the formation of the two radicals (33) and ( 3 4 ) , the three possible products (36)- (38) of their combination also being isolated. Cyclopropanations with phosphoryldiazoalkanes by the carbenoid route are more clear-cut and usually give a very high yield (Table 3); the H-abstraction that dominates on photochemical production of the carbenes is wholly suppressed.…”

Section: Intermolecular Reactions[*'mentioning

confidence: 99%

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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Section: Intermolecular Reactions[*'mentioning

confidence: 99%