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Über cyclische β‐Diketone. 3. Mitteilung. Die Methylierung von (±)‐ cis ‐ und (±)‐ trans ‐Decalindion‐(1,3), sowie von (±)‐2‐Methyl‐ trans ‐decalindion‐(1,3) mit Diazomethan
Author(s) -
Mühle H.,
Tamm Ch.
Publication year - 1962
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.19620450513
Subject(s) - chemistry , diazomethane , stereochemistry , ether , medicinal chemistry , organic chemistry
On treatment with diazomethane in ether‐methanol (2 hours at 20°), (±)‐ trans ‐decalin‐1, 3‐dione (V) yields (±)‐3‐methoxy‐ trans ‐Δ 2 ‐octalin‐1‐one (VII) and (±)‐1‐methoxy‐ trans ‐Δ 1 ‐octalin‐3‐one (IX) in a ratio of 2:1. Methylation in the cis ‐series gives the analogous products XVI and XVIII in the same ratio. The structure of the four isomeric enol‐methylethers VII, IX, XVI and XVIII is proven by their conversion into the corresponding α,β‐unsaturated octalenones and the saturated decalones.