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ISBN-10: 0470318910

ISBN-13: 9780470318911

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Liu, J . Am, Chem. , 91,6909 (1969); H. T. , p. 6911. 40/, of endo-benzonorbornen-2-ylbromide. The exobromide from the addition of DBr is 37% deuterated at position 7 and the remainder presumably a t position 3. All the deuterium in the endo-formis at position 3. Q2 Stable Phenonium Ions When a 3-aryl-2,3-dimethyl-2-butyl chloride (114) or an aryl-t-butyl-methylcarbinyl chloride (115) is dissolved in SbF6-S02a t -78” the same carbonium ions are formed but the nature of these depends on the aryl group (p-XCsH4).

Farkas, Tetrahedroii, 24,6773 (1968). 65 U. J. Lancelot a d P. yon R. Schloyer, J. Am. Chem. , 91, 4291 (1969). 62 63 M. aa Oryunic Reeuclioii Mechunivnis 1969 against u*. g. 86 for acetolysis at 100' and formolysis at 76"respectively, but the points for the compounds with X = H, p-Me, and p-Me0 fell above the lines so defined. se The third approach involved an investigation of the solvolysis of compounds (89). Clearly the effects of the substituents X and Y should be additive if the ary1rings influenced the rates solely through inductive effects, but since only one ringcan participate at any one time they should not be when there is participation.

The formation of twice as much cis-isomer (207) a8 of transisomer (208) was attributed to the intervention of an ion-pair. 136 Deamination of 3-methyl[l,l-2H2]but-3-enylamine yields l-methylcyclobutanol (yield unstated) with all the deuterium at position 3 (equation 11). ls7 135 S. A. Roman and W. D. Closson, J . Am. Chem. , 91, 136 P. K. Freeman, F. A. Raymond. and J. N. Blazevich, J . 1701 (1969). Org. , 84,1176 (1060). 137 W. B. Kover and J. D. Roberta, J . Am. Chem. , 91,3687 (1969). 45 Carboriiurn l o t u ..

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Organic Reaction Mechanisms 1969


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