Issue 12, 1991
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Hypervalent organoiodine compounds: radical fragmentation of oxabicyclic hemiacetals. Convenient synthesis of medium-sized and spiro lactones

María T. Arencibia,   Raimundo Freire,   Aurea Perales,   María S. Rodríguez  and  Ernesto Suárez  

Abstract

Photolysis of steroidal models of oxyabicyclic hemiacetals such as 2-oxabicyclo[4.4.0]decan-1-ol, 9-oxabicyclo[4.3.0]nonan-1-ol and 2-oxabicyclo[3.3.0]octan-1-ol, in the presence of (diacetoxyiodo)benzene and iodine afforded, through ring expansion, ten-, nine- and eight-membered lactones, respectively. Spiro lactones of dihydropyran-5-spirocyclohexan-2(3H)-one and dihydrofuran-4-spirocyclohexan-2(3H)-one types were obtained by photolysis of steroidal models of 2-oxabil cyclo[2.2.2]octan-1 -ol and 7-oxabicyclo[3.2.1 ]octan-1 -ol, respectively.

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Article information

DOI
https://doi.org/10.1039/P19910003349
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 3349-3360

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Hypervalent organoiodine compounds: radical fragmentation of oxabicyclic hemiacetals. Convenient synthesis of medium-sized and spiro lactones

M. T. Arencibia, R. Freire, A. Perales, M. S. Rodríguez and E. Suárez, J. Chem. Soc., Perkin Trans. 1, 1991, 3349 DOI: 10.1039/P19910003349

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