Reduced-symmetry Deep-cavity Cavitands

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3845-3848

  Green, Jodie O ^a   Baird, John Henry ^a   Gibb, Bruce C ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001302062     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006569m     Document Type: Article

References (24)

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18. This value assumes no intermolecular bridging between the mono-, bis-, and trisbridged intermediates.
19. These findings may indicate that the bridging route from octol to DCC primarily involves an A/B-bisbridged intermediate. Such an apparent preference could be attributed to the degree of preorganization of the resorcinol rings. Thus, the introduction of the first bridge, e.g., to form 2a, results in the preorganization of one of the resorcinol rings if the next bridge is to go to the B position (e.g., to form 3a) but does not preorganize the resorcinol rings involved with the second bridge going in to the C position (e.g., to form 4a). Alternatively, these results might indicate different rates of decomposition of 3a and 4a in the reaction medium. However if this were the case then it would be expected that yields for the conversion of 3b into 6b/12 and 4b into 6b/13 (see text) would differ. This was not observed.
20. The isolation of comparable yields of tris-bridged products arising from nonstereospecific bridging processes has been attributed to a relatively high energy barrier when introducing the fourth bridge. See ref 6.
21. Thirteen reactions gave an average ratio of 3b to 4b of 7.55 (±σ = 3.0). For the six reactions that share the same solvent and base similar, statistically significant results were noted (3b:4b ratio of 6.11 ± σ = 1.3). Both of these results are statistically significantly greater than the expected 2:1 ratio.
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