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Photochemistry of bicyclo[3.3.1]nonenes

โœ Scribed by M. Kawanisi; H. Kato


Book ID
104248671
Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
127 KB
Volume
11
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Recent report (1) on photochemical polar addition reaction of methanol or 2propanol to a bridged bicyclic olefin, bicyolo(3.2.l)oct-2-ene, has prompted US to report results on the polar addition of acetic acid to the similar system, bicyclo(3.3.l)non-2-ene and its derivative, possibly accompanying 3,7-hydride shift.

When a 1% acetic acid-benzene solution of I wae irradiated with unfiltered high premsure mercury arc for 48 hr under atmosphere of N2, two isomerio adducts,


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Synthesis and Structure of Phenylโ€Substituted Bicyclo[3.3.1]nonenes Addition of one mole of phenyllithium to bicyclo[3.3.1]nonaneโ€2,6โ€dione (5) affords the hydroxy ketone 6 besides small amounts of the known diol 7. Dehydration of this mixture by sulfuric acid in acetic acid yields the unsaturated