Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin- 2-ylidene bromides and rearrangement reaction thereof

Synlett

Volumn , Issue 5, 2000, Pages 607-610

  Marković, Rade ^a   Baranac, Marija ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

4 oxothiazolidine derivatives; Push pull alkene; Rearrangement reaction; Regioselective bromination

Indexed keywords

BROMINE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL BOND; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034072952     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

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14. AB =17.2 Hz) and 11.63 (s, lactam H) assigned to the minor dibromide 6; proportions of 3c:6 (ca. 80:20) were deduced from the relative intensities of the lactam singlets at δ 11.46 and 11.63 ppm respectively. (matrix presented)
15. 3): δ 14.1, 35.6, 37.7, 41.4, 44.0, 61.6, 85.3, 126.7, 128.8, 138.4, 151.4, 163.1, 170.2, 173.9.
16. 4.
17. It should be recognized that the configurational stability of E-geometrical isomers 3a-c should be also attributed to attractive electrostatic oxygen-sulfur interactions, as depicted below (see, in addition, ref. 2 and 12). (matrix presented)
18. 1H NMR chemical shift differences for lactam NH proton (Δδ ∼ 3.3 to 3.5 ppm between Z and E-isomers 3b-c) may serve as a useful reference in assisting the stereochemical characterization of C=C double bonds in similar compounds.
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22. 4S: C, 58.94; H, 5.24; N, 8.09; S, 9.26. Found C, 59.15; H, 5.28; N, 8.38; S, 9.51.