Fragmentation of homoallylic alkoxides. Synthesis of propenyl and 2-methylpropenyl ketones from carboxylic esters
β 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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π SIMILAR VOLUMES
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).
## Abstract The potassium 2βsubstituted bicyclo[2.2.1]heptβ5βenβ2βalkoxides derived from alcohols **2β9** at 30Β° in hexamethylphosphoric triamide (HMPA) afford 1β(3β²βcyclopentenyl)β2βalkanones **10β19** __via__ heterolytic C(1), C(2)βallylic bond cleavage in the substrate alkoxide followed by intra
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]).
Reaction of Carboxylic Esters and in situ Generated Carboxamides Yielding ## Kerones Ketone/alcohol