Transmission of electronic substituent effects in 4-substituted bicyclo[2.2.2]octyl systems
โ Scribed by Adcock, William; Butt, Graeme; Kok, Gaik B.; Marriott, Stephen; Topsom, Ronald D.
- Book ID
- 126988291
- Publisher
- American Chemical Society
- Year
- 1985
- Tongue
- English
- Weight
- 839 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0022-3263
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๐ SIMILAR VOLUMES
Hydrolysisofbicyclo[2.2.2]octylp-nitrobenzenesulfonate (14a,X =p-N02C6H4S03), and nineteen 4-R-substituted derivatives 14b-14 t in 70% aqueous dioxane yield the corresponding bicyclo [2.2.2]octanols 14 (X = OH), exclusively. The 7-center fragmentation to 1,4-dimethylidene-cyclohexane (15) is not obs
H/lH isotope effects on the "F chemical shifts of 4-substituted bicyclo[2.2.2]octl-y1 and bicyclo[2.2.l]hept-l-y1 fluoride are significantly shielding and deshielding, respectively. This result is consistent with deuterium being viewed as an electronegative substituent relative to hydrogen when atta