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Synthese und B ECKMANN ‐Umlagerung von 1‐Acetyl‐bicyclo [2.2.2] octan‐oxim. Bicyclo [2.2.2] octan‐Reihe, 8. Mitteilung
Author(s) -
Fischer H. J.,
Grob C. A.
Publication year - 1964
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.19640470223
Subject(s) - chemistry , bicyclic molecule , octane , medicinal chemistry , stereochemistry , organic chemistry
The synthesis of 1 ‐acetyl‐bicyclo[2.2.2]octane oxime is described. The p ‐toluene‐sulfonic ester of this compound affords l‐acetamido‐bicyclo[2.2.2]octane ( 7 ) upon B ECKMANN rearrangement, and therefore possesses the anti ‐R/OTs configuration 6 .1 ‐Acetamido‐bicyclo[2.2.2]octane ( 7 ) is also obtained by the H OFMANN reaction of l‐carbamoyl‐bicyclo[2.2.2]octane ( 3 ).
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