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Preparation of 1,2exo- and 1,2endo-Diiodo-bicyclo[2.2.1]heptane

✍ Scribed by Hugo Camenzind; Ernst-Peter Krebs; Reinhart Keese

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
399 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

1,2 exo‐Diiodo‐norbornane (4) was prepared from norcamphor hydrazone by oxidative iodination and subsequent rearrangement of the 2,2‐diiodo‐bicyclo [2.2.1]heptane (2). The stable α‐iodohydrazone 11 was obtained from 1‐iodo‐bicyclo[2.2.1]heptan‐2‐one (10), which itself was prepared from 1‐iodo‐norbornene (5). Subsequent treatment of 11 with iodine lead to 1,2,2‐triiodo‐norbornane (12) and l,2‐diiodo‐norborn‐2‐ene (13). 1,2 endo‐Diiodo‐norbornane (14) was obtained by stereoselective reduction of 12 with tribtityltinhydride or by reaction of 13 with diimide.

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exo/endo-Selectivity in the Reaction of
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