Helvetica Chimica Acta p. 2042 - 2048 (1982)
Update date:2022-08-03
Topics:
Camenzind, Hugo
Krebs, Ernst-Peter
Keese, Reinhart
1,2exo-Diiodo-norbornane (4) was prepared from norcamphor hydrazone by oxidative iodination and subsequent rearragement 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 1,2-diiodo-norborn-2-ene (13). 1,2endo-Diiodo-norbornane (14) was obtained by stereoselective reduction of 12 with tributhyltinhydride or by reaction of 13 with diimide.
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Doi:10.1021/jo00159a008
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(1960)
