Controlling the regioselectivity of lithiation using kinetic isotope effects: Deuterium as a protecting group for carbon

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8377-8380

  Clayden, Jonathan ^a   Pink, Jennifer H ^a   Westlund, Neil ^a   Wilson, Francis X ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMIDE; BENZAMIDE; CARBAMIC ACID; DEUTERIUM; HYDROGEN; LITHIUM;

CHEMICAL REACTION; KINETICS; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 0032511947     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01930-3     Document Type: Article

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18. 13. Magnitudes of the KIE for such directed lithiation reactions have been published only for the ortholithiation of anisole: Stratakis, M. J. Org. Chem. 1997, 62, 3024 (but see also Shatenshtein, A. I. Tetrahedron 1962, 18, 95). For kinetic isotope effect studies on lithiation a to heteroatoms, see references 3, 11 and 12(b).
19. 13. Magnitudes of the KIE for such directed lithiation reactions have been published only for the ortholithiation of anisole: Stratakis, M. J. Org. Chem. 1997, 62, 3024 (but see also Shatenshtein, A. I. Tetrahedron 1962, 18, 95). For kinetic isotope effect studies on lithiation a to heteroatoms, see references 3, 11 and 12(b).
20. 14. Similarly large values have been observed before and attributed to quantum tunnelling effects: see ref. 11.
21. D which is too low.
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