1973
DOI: 10.1016/s0040-4039(01)86896-9
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The effect of 1,5-bridging on the solvolytic behavior of the bicyclo[3.1.0]hex-2-yl cation

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Cited by 13 publications
(10 citation statements)
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“…The x-ray structure (see Figure 1 for a drawing of the final model) shows that the conformation of the nine-membered ring of 19 closely resembles the "twisted chair boat" (TCB) conformation found for cyclononylamine hydrobromide11 and cyclononanone. 12 The bond angles in all three structures generally agree; however, the average bond distances for the medium ring of 19 are significantly shorter (mean value 1.513 Á) than those for both cyclononylamine hydrobromide (mean value 1.532 Á) and cyclononanone (mean value 1.533 Á).…”
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confidence: 78%
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“…The x-ray structure (see Figure 1 for a drawing of the final model) shows that the conformation of the nine-membered ring of 19 closely resembles the "twisted chair boat" (TCB) conformation found for cyclononylamine hydrobromide11 and cyclononanone. 12 The bond angles in all three structures generally agree; however, the average bond distances for the medium ring of 19 are significantly shorter (mean value 1.513 Á) than those for both cyclononylamine hydrobromide (mean value 1.532 Á) and cyclononanone (mean value 1.533 Á).…”
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confidence: 78%
“…5-Bromomethylenecyclononanone (3): 21 mg (5.4%). d. l,6-Diacetoxy-10a-bromobicyclo[4.3.1]decane (20): 299 mg (53%), mp73-74 °C (hexane); IR (CC14) 1730, 1250cm-1; NMR already reported;4f l3C NMR (CDC13) 169.6, 124.4, 83.9,66.2,38.1, 36.3, 22.4, 20.9; mass spectrum (16 eV) parent ion not detected (m/e 332), but observed were peaks at m/e (rel int) 232 (4, P -Ac20), 230 (4, P -Ac20), 214 (17), 212 (17), 203 (6), 201 (6), 190 (19), 188 (19), 151 (95), 133 (37), 43 (100). Anal.…”
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confidence: 99%
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