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Small-Ring Compounds. XXVIII. Isotope-Position Rearrangements of Allylcarbinyl Grignard Reagents

Silver, Marc S. and Shafer, Paul R. and Nordlander, J. Eric and Rüchardt, C. and Roberts, John D. (1960) Small-Ring Compounds. XXVIII. Isotope-Position Rearrangements of Allylcarbinyl Grignard Reagents. Journal of the American Chemical Society, 82 (10). pp. 2646-2647. ISSN 0002-7863.

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We have observed a remarkable rearrangement while attempting to prepare 4-penten-2-ylarnine (I) through the reaction of the Grignard reagent derived from 4-penten-2-yl chloride (II) with methoxylamine, in that part of the amine formed appeared to be 2-methyl-3-butenylamine (III).

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Additional Information:© 1960 American Chemical Society. Received April 9, 1960. Supported in part by the Office of Naval Research and the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is hereby made to the donors of the Petroleum Research Fund. Presented in part at the Sixteenth National Organic Symposium, Seattle, Washington, June 15, 1959.
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Office of Naval Research (ONR)UNSPECIFIED
American Chemical Society Petroleum Research FundUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2570
Issue or Number:10
Record Number:CaltechAUTHORS:20151020-124117005
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Official Citation:SMALL-RING COMPOUNDS. XXVIII. ISOTOPE-POSITION REARRANGEMENTS OF ALLYLCARBINYL GRIGNARD REAGENTS Marc S. Silver, Paul R. Shafer, J. Eric Nordlander, C. Rüchardt, and John D. Roberts Journal of the American Chemical Society 1960 82 (10), 2646-2647 DOI: 10.1021/ja01495a068
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61335
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 20:57
Last Modified:03 Oct 2019 09:06

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