Journal of Organic Chemistry p. 2200 - 2201 (1981)
Update date:2022-08-16
Topics:
Stephenson, L. M.
Orfanopoulos, Michael
Inter- and intramolecular isotope effects for both thermal and SnCl4-catalyzed ene reactions of oxomalonic esters have been measured.Primary isotope effects are high (ca. 3.3) in thermal reactions and negligible (ca. 1.1) in SnCl4-catalyzed cases, even where intramolecular competitions are available.A concerted mechanism with variations in C-C bond formation and C-H(D) bond breaking is proposed.A potentially useful cyclization reaction is also described.
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Doi:10.1021/ja01298a004
(1936)Doi:10.1246/cl.1980.1493
(1980)Doi:10.1021/jf60121a014
(1962)Doi:10.1021/ja00388a037
(1982)Doi:10.1246/bcsj.53.3721
(1980)Doi:10.1007/BF00779218
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