References
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- Glaze , W. H. 1970 . Organometal. Chem. Revs., B , 6 : 1 See, for example and 8, 253 (1971)
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- Slocum , D. W. , Boyle , G. and Jennings , C. H. 1970 . Tetrahedron Lett. , : 3443 See also
- Paust , J. and Schöllkopf , U. 1965 . Angew. Chem. Int. Ed. Engl. , 4 : 246
- Schöllkopf , U. , Paust , J. , Ali-Azrak , A. and Schumacher , H. 1966 . Chem. Ber. , 99 : 3391
- Schöllkopf , U. 1968 . Angew. Chem. Int. Ed. Engl. , 7 : 588
- Schöllkopf , U. , Paust , J. and Patsch , M. R. 1969 . Org. Syntheses , 79 : 86
- Sliwinski , W. F. , Su , T. M. and von Schleyer , P. R. 1972 . J. Amer. Chem. Soc. , 94 : 133 and references therein
- Schöllkopf , U. , Fellenberger , K. , Patsch , M. , von Schleyer , P. R. , Su , T. and Van Dyne , G. W. 1967 . Tetrahedron Lett. , : 3639
- Normant , J. F. , Cahiez , G. , Chuit , C. and Villieras , J. 1973 . Tetrahedron Lett. , : 2407
- Although lithium exchange with chlorine is slower than exchange with bromine or iodine (ref. 3b), there are reports of lithium-chlorine exchange
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- Wittig , G. and Wirt , H. 1941 . Chem. Ber. , 74 : 1474
- Ager , E. , Iddon , B. and Suschitzky , H. 1969 . Tetrahedron Lett. , : 1507
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- Paul , R. and Riobe , O. 1947 . C. R. Acad. Sci. , 224 : 475 Fragmentation of β-alkoxyethylsodium and β-alkoxyethylchromium species is reported to produce alkenes: J. K. Kochi, D. M. Singleton, and L. J. Andrews, Tetrahedron, 24, 3503 (1968)
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- Analogously, lithium ethoxide is produced by n-butyllithium induced fragmentation of diethyl ether (see ref. 3b):
- Baldwin , J. , Hofle , G. A. and Lever , O. W. Jr. 1974 . J. Amer. Chem. Soc. , 96 : 7125 The reaction scheme shown below is consistent with the need for ≥ 3 equiv of n-butyllithium and with the formation of an alkyne from the β-chloroethyl group: This mechanism, however involves the intermediacy of a vinyl ether. Vinyl ethers of type i, R'=H, are unreactive toward n-butyllithium and are not converted to alkynes but rather are metalated by tert-butyllithium to form i, R'=Li and U. Schollkopf and P. Hannsle, Ann., 763, 208 (1972).] This dechloroethylation mechanism, therefore, seems unlikely, even for i, R'=n-C12H23
- March , J. 1968 . “ Ch. 9 ” . In Advanced Organic Chemistry , New York, N. Y. : McGraw Hill Book Co. .
- Dermer , O. C. and Ham , G. E. 1969 . Ethyleneimine and Other Aziridines: Chemistry and Applications , New York, N. Y. : Academic Press .
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- Paul , R. and Tchelitcheff , S. 1954 . C. R. Acad. Sci. , 238 : 2089 β-Chloroethyl(diethyl)amine reacts with metallic sodium to form diethylamine (via dechloroethylation), triethylamine, and bis-1,2-dimethylaminoethane in 30, 30, and 12% yields, respectively
- Gurien , H. 1963 . J. Org. Chem. , 28 : 878 Reaction of a β-chloroethylamine with a magnesium dimethylamide proceeds via chlorine displacement to form a β-(dimethylamine) ethylamine product
- Kochi , J. K. , Singleton , D. M. and Andrews , L. J. 1968 . Tetrahedron , 24 : 3503 Chromous ions are reported in two cases to cause dechloroethylation of some β-chloroethyl amines
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- Bakke , J. , Feil , V. J. , Zaylskie , R. G. and Thacker , E. J. Federation Proceedings . Vol. 30 , pp. 387 An in vivo dechloroethylation of cyclophosphamide, a bis(chloro-ethyl)amine, has recently been reported: abstract number 1089
- Egloff , G. , ed. Physical Constants of Hydrocarbons , ACS Monograph Series Vol. I ,
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