The Effect of Changing Reagent upon Stereoselectivity 1a
Journal Article
·
· Journal of the American Chemical Society
The stereoselectivities exhibited during several reactions in which a second, adjacent asymmetric carbon atom is formed were observed. The effect of changing the organometallic reagent from phenyllithium to phenylmagnesium iodide to pherylmagnesium bromide to phenylmagnesium chloride was also studied in the addition of these reagents to biacetyl or to phenylacetoin. It was shown that the product dl: meso ratio is greater than one when either phenyllithium or phenylmagnesium iodide is eraployed, and less than one when phenylinagnesium bromide or chloride is employed. A similar series of reactions between benzil or methylbenzoin and the corresponding methyl reagents is also reported. All results are discussed in terms of the hypothetical intermediates.
- Research Organization:
- Oak Ridge National Lab., Tenn.
- Sponsoring Organization:
- USDOE
- NSA Number:
- NSA-14-022823
- OSTI ID:
- 4153250
- Journal Information:
- Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 15 Vol. 82; ISSN 0002-7863
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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