Preparation of 1,2exo- and 1,2endo-Diiodo-bicycloheptane

Article abstract of DOI:10.1002/hlca.19820650711

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.