References
- On leave, Institute of Elemento Organic Chemistry, Nankai University, Tientsin, Peoples' Republic of China 1980–1981
- Seebach , D. and Geiss , K ‐H. 1976 . “ New Applications of Organometallic Reagents in Organic Synthesis ” . In Organometallic Chemistry Library 1 , Edited by: Seebach , D. 21 – 26 . Amsterdam : Elsevier Publishing Co. .
- Still , W. C. and Macdonald , T. L. 1976 . J. Org. Chem. , 41 : 3620
- Pohmakotr , M. , Geiss , K ‐H and Seebach , D. 1979 . Chem. Ber. , 112 : 1420
- Geiss , K. H. , Seebach , D. and Seuring , B. 1977 . Chem. Ber. , 110 : 1833
- Carlson , R. M. 1978 . Tetrahedron Lett. , 2 : 111
- Carlson , R. M. , White , L. L. and Meyer , F. K. to be published
- Martinez , S. J. and Toule , T. A. 1978 . Tetrahedron , 34 : 3027 The isomerization reported herein bears some similarity to the reported isomerization of 3° allylic amines to enamines, see, and references therein
- Hänssgen , D. and Odenhauser , E. 1979 . Chem. Ber. , 112 : 2389 These results are in contrast to those observed with other 2° allyl amines which, depending on the reaction conditions, have been found to undergo addition or to form the vinyl amide dianion, see
- Wender , P. A. and Schaus , J. M. 1978 . J. Org. Chem. , 43 : 782 and references therein
- 20MHz C‐13 NMR: °c(ppm) 161
- House , H. O. 1974 . Modern Synthetic Reactions , 2nd Ed. , 89 – 93 . New York , N. Y. : W. A. Benjamin Inc. . Prepared by the lithium aluminum hydride reduction of the formamide (optimum time‐4 hrs/ether) which, in turn, had been generated by refluxing the amine in a 10‐fold excess of ethyl formate. The products always indicated a certain amount of reduction of the double bond in a manner similar to that reported for allylic alcohols see:
- Weston , A. W. , Ruddy , A. W. and Sater , C. M. 1943 . J. Amer. Chem. Soc. , 65 : 674 An independent synthesis was performed using the allylic sulfonamide anion and methyl iodide in a similar manner to that described by:
- Wittig , G. and Suchanek , P. 1963 . Agnew, Chem. Int. Ed. , 2 : 683 m. p. 82–82°