Scientific article

Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane

Published inHelvetica chimica acta, vol. 56, no. 3, p. 1083-1096
Publication date1973-04-25

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%.

Citation (ISO format)
JEFFORD, Charles, BURGER, Ulrich, DELAY, François. Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane. In: Helvetica chimica acta, 1973, vol. 56, n° 3, p. 1083–1096. doi: 10.1002/hlca.19730560329
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Article (Published version)
ISSN of the journal0018-019X

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