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Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane
Author(s) -
Jefford Charles W.,
Burger Ulrich,
Delay François
Publication year - 1973
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.19730560329
Subject(s) - bicyclic molecule , chemistry , dichlorocarbene , nonane , ene reaction , yield (engineering) , adduct , octane , sodium methoxide , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
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%.