59. “Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane”
    Jefford, C.W.; Burger, U.; Delay, F.
    Helv. Chim. Acta 1973, 56, 1083-1096.

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%.

DOI : 10.1002/hlca.19730560329 

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