We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane.
- Authors
Jefford, Charles W.; Burger, Ulrich; Delay, François
- Abstract
The addition of dichlorocarbene (generated by the interaction of sodium methoxide and ethyl trichloroacetate) to bicyclo[3.2.1]oct-2-ene, its 3-chloro and exo-3,4-dichloro derivatives gives the exo 1 : 1 adducts in yields of 94, 89 and 48%. By suitable chemical reactions of these adducts, convenient syntheses of bicyclo[4.2.1]nona-2,4-diene and bicyclo[4.2.1]non-3-ene, together with their monochloro, dichloro and trichloro derivatives are obtained. Bicyclo[4.2.1]-nonan-3-one is also obtained from bicyclo[4.2.1]non-3-ene in a synthesis starting from the readily available 5-hydroxymethylnorborn-2-ene in an overall yield of 20%.
- Publication
Helvetica Chimica Acta, 1973, Vol 56, Issue 3, p1083
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19730560329