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Acetolysis of 4‐ endo ‐diazoacetyl‐bicyclo[3.1.0]hexene: a new synthesis of semibullvalene. Preliminary communication
Author(s) -
Malherbe Roger
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.19730560819
Subject(s) - chemistry , bicyclic molecule , yield (engineering) , 1 hexene , sequence (biology) , stereochemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy , ethylene
Acetolysis of diazoketone 1 gives in good yield 6‐acetoxy‐tricyclo[3.3.0.0 2,8 ]octan‐3‐one ( 2 ) which is converted into semibullvalene in a three‐step sequence. Compound 2 is potentially a good starting material for 3,6‐substituted semibullvalenes.