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Adamantane rearrangement of [3.3.2]propellanes

โœ Scribed by Tobe, Yoshito; Terashima, Kaoru; Sakai, Yasuo; Odaira, Yoshinobu


Book ID
121304212
Publisher
American Chemical Society
Year
1981
Tongue
English
Weight
401 KB
Volume
103
Category
Article
ISSN
0002-7863

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The acid-catalyzed rearrangements of three model tricyclo[4.3.2] propellane derivatives have been explored. In each case the observed products are proposed to arise via a concerted 1,2-shift of the cyclobutane bond having an antiperiplanar alignment with the leaving group (i.e., stereoelectronic con

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## Abstract 3,7,10โ€Tribenzylโ€3,7,10โ€triaza[3.3.3]propellane (**4a**), 3,7โ€dibenzylโ€10โ€phenylโ€3,7,10โ€triaza[3.3.3]propellane (**4c**), 3,7โ€dibenzylโ€10โ€(__p__โ€tolyl)โ€3,7,10โ€triaza[3.3.3]propellane (**4b**), and 3โ€oxaโ€7,10โ€diaza[3.3.3]propellane (**6**) have been prepared.

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## Abstract From treatment of Dโ€labelled 1, 2__exo__โ€, 1, 2__endo__โ€ and 2__endo__, 6__endo__โ€trimethyleneโ€norbornane (**1, 2** and **3**, resp.) with aluminum bromide in carbon disulfide, the evidence is gained that a degenerate rearrangement is involved in the admantane rearrangement of both **1*

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The title compound was prepared by transammlar addition of a carbene to an exocyclic double bond. Rhodium acetate catalyzed decomposition of 2-diazo-&methylene-1,3-cyclooctanedione gave 1 quantitatively. We wish to report the first synthesis of the title compound, 1, and a new approach to propellan