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Reductive cleavage of 1-methyltricyclo[4.4.0.02,6]Decan-3-one and related compounds with lithium in liquid ammonia

✍ Scribed by Drury Caine; William R. Pennington; Troy L. Smith Jr.

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
288 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reductive cleavage of the external(a.8) bond of the cyclopropane ring in tricyclo[x.y.O.O *,x9_ alkan-3-ones with lithium in liquid ammonia provides a general method of synthesis of spirocyclic ketones. *,3 Piers and Worster have recognized that the stereochemical fate of the S carbon atom is an important feature of these reactious.3 They conducted a detailed study of the reaction of cis-1,7-dimethyltricyclo[4.4.0.0 -*+d ecan-3-one (&a> with lithium in liquid ammonia and found that the trans dimethyl ketone & (inversion of configuration at the f3 carbon) was favored over the cis isomer & (retention at the S position) under a variety of conditions. At -78' and with no added proton donor or up to 5 equiv of an added alcohol the &:& ratio was 9:l or greater. We have A.

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