ChemInform Abstract: STEREOCHEMISTRY OF THE ELECTROPHILIC RING OPENING OF CYCLOPROPANES BY D(+). EVIDENCE FOR AN UNSYMMETRICAL, NONROTATING, CORNER‐PROTONATED CYCLOPROPANE

DePuy, Charles H.; Andrist, A. Harry; Fuenfschilling, Peter C.

doi:10.1002/chin.197416153

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-45°01

Copaanes Copabornanes Ylanganes and Sativanes1

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1976

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“…A recent publication by DE PuY, ANDRIST, and FüNFSCHILLING reports upon the stereochemistry of the electrophilic ring opening of cis and trans 1 ,2,3-trimethylcyclopropane with deuterated acids (196,197). While the attack of the entering nucleophile occurred with essentially complete inversion, the overall stereochemistry of protonation took place with both retention (68%) and inversion (32%).…”

Section: -45°0mentioning

confidence: 95%

“…. cts The stannic chloride-catalyzed cyclization of acyl cyclopropane (195) to the tricyclic ketone (196) affords a precedent for the biogenesis of the tricyclo[4.4.0.0Z· 7 ]nucleus of copaene and ylangene (270). The reaction pathway is thought to proceed via ring opening, cyclization, hydride shift, and ring closure.…”

Section: Copaanes Copabornanes Ylanganes and Sativanesmentioning

confidence: 99%

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