Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Stereochemical Studies on the Nucleophilic Substitution in the Reaction of Allylic Phosphates with Organoaluminum Reagents
Akira ItohShuji OzawaKoichiro OshimaShizuka SasakiHajime YamamotoTamejiro HiyamaHitosi Nozaki
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1980 Volume 53 Issue 8 Pages 2357-2362

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Abstract

The reaction of cis- or trans-5-isopropenyl-2-methyl-2-cyclohexenyl diethyl phosphate (1) with Me2AlX (X=OPh, SPh, NHPh) in hexane results in substitution of the –O–PO(OEt)2 group with X under predominant inversion. In contrast, treatment of cis- or trans-1 with trialkylaluminum produces predominantly the allyl-nonallyl couplingproducts of the same (thermodynamically more stable) configuration. Similar alkylation of endo- and exo-2-acetoxynorcarane gave endo-2-methylnorcarane, exclusively.

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