REARRANGEMENTS INVOLVING THE TRICYCLO[3.1.1.0(3,6)]HEPTYL AND TRICYCLO[3.2.1.0(3,6)]OCTYL SYSTEMS - SINGLE-ELECTRON TRANSFER IN THE REDUCTION OF A BRIDGEHEAD TOSYLATE WITH LITHIUM ALUMINUM-HYDRIDE

The attempted conversion of tricyclo[3.1.1.0(3,6)]heptane-6-methanol (9) into the corresponding tosylate (7) leads instead to a rearranged isomer tricyclo[3.2.1.0(3,6)]oct-6-yl tosylate (10). Treatment of (10) with lithium aluminium hydride affords a mixture of the parent alcohol tricyclo[3.2.1.0(3,...

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Bibliographic Details
Published inAustralian journal of chemistry Vol. 45; no. 8; pp. 1205 - 1211
Main Authors DELLA, EW, JANOWSKI, WK, PIGOU, PE
Format Journal Article
LanguageEnglish
Published COLLINGWOOD C S I R O PUBLICATIONS 01.01.1992
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
IODIDES
LIALH4
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Summary:The attempted conversion of tricyclo[3.1.1.0(3,6)]heptane-6-methanol (9) into the corresponding tosylate (7) leads instead to a rearranged isomer tricyclo[3.2.1.0(3,6)]oct-6-yl tosylate (10). Treatment of (10) with lithium aluminium hydride affords a mixture of the parent alcohol tricyclo[3.2.1.0(3,6)]octan-6-ol (15) and endo-bicyclo[3.2.1]octan-6-ol. The available evidence suggests that the latter arises by a process which appears to be mediated by alkoxy radicals rather than anions.
ISSN:0004-9425
DOI:10.1071/CH9921205