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Fragmentation of homoallylic alkoxides. Synthesis of propenyl and 2-methylpropenyl ketones from carboxylic esters

✍ Scribed by Roger L. Snowden; Bernard L. Muller; Karl H. Schulte-Elte


Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
191 KB
Volume
23
Category
Article
ISSN
0040-4039

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πŸ“œ SIMILAR VOLUMES


Ξ²-Cleavage of Bis(homoallylic) Potassium
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Products isolated by column chromatography on silica gel (cf: Euper. PurtJ ; compositions of tautomeric mixturcs measured at 25"; in CDCI, solution, by 'H-NMR (360 MHL) spectroscopy. b, Yield from y-butyrolactone (1). ') Yicld from 6-valerolactone (2). \*) Yicld from 3-methyl-6-valerolactone (3).

Fragmentation of Homoallylic Alkoxides.
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## Abstract The potassium 2‐substituted bicyclo[2.2.1]hept‐5‐en‐2‐alkoxides derived from alcohols **2–9** at 30Β° in hexamethylphosphoric triamide (HMPA) afford 1‐(3′‐cyclopentenyl)‐2‐alkanones **10–19** __via__ heterolytic C(1), C(2)‐allylic bond cleavage in the substrate alkoxide followed by intra

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For a special (intramolecular) case, see [5]. Vol.69 (1986) 229 ') The diethylamides corresponding to esters 1-3 are unreactive. ( E ) / ( Z ) % 9:l. We assume that the major silylenol ether 12 formed has the (E)-configuration (see [15]).