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Preparation of 1,2 exo ‐ and 1,2 endo ‐Diiodo‐bicyclo[2.2.1]heptane
Author(s) -
Camenzind Hugo,
Krebs ErnstPeter,
Keese Reinhart
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650711
Subject(s) - norbornane , chemistry , bicyclic molecule , norbornene , heptane , bridged compounds , medicinal chemistry , halogenation , stereochemistry , organic chemistry , monomer , polymer
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.