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Synthesis of [4.3.3] Propellanes by the photochemical addition of tetralin to olefins

✍ Scribed by C.S. Angadiyavar; J. Cornelisse; V.Y. Merritt; R. Srinivasan

Book ID
104238566
Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
136 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis

has been pointed out '** that the photochemical 1,3-additions of alkylbenzenes to cyclic show a high degree of orientational specificity. Thus, the addition of g-xylene to cyclopentene yields I and II in the ratio of 3:l as the only products although six such adducts (with endo fusion of the cyclopentane ring) are theoretically possible.

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## Abstract Treatment of (+)‐sclareolide (**1**) with polyphosphoric acid or __Eaton'__s reagent furnished, besides the anticipated cyclopentenone (βˆ’)‐**12** and its isomer (βˆ’)‐**15**, two diastereoisomeric [4.3.3]propellanes (βˆ’)‐**13** and (βˆ’)‐**14**, which possess interesting woody‐ambery odors.