ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Two new syntheses of spiro[4.4]nonane-1, 6-dione (I) are described: one by rearrangement of 1,6-epoxy-bicyclo[4.3.0]-nonane-2-one (IV) with boron trifluoride, the other by an acid catalyzed, intramolecular Claisen condensation of 4-(2-oxocyclopentyl)-butyric acid. Spiro[4.4]-nonane-1,6-dione is converted into trans, trans-spiro[4.4]nonane-1,6-diol which is resolved into enantiomers via the diastereomeric esters with (-)-camphanic acid. (+)-(5S)-Spiro[4.4]nona-1,6-diene (III) is prepared from (1R, 6R)-trans,trans-spiro[4.4]nonane-1,6-diol (II) by pyrolysis of the corresponding bis-4-methylphenyl-thionocarbonate. This modification of the Chugaev reaction is particularly useful with sterically hindered alcohols which cannot be converted into S-me-thylxanthates. The circular dichroism, UV.- and NMR.-spectrum of optically active spiro[4.4]-nonane-1,6-diene are discussed.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19720550702
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