~a&~$&iU~~ion lq June 1972) (Received in USA 16 Play 1972; rece:ved in The mechanism of solvolysis of Z-adamantyl derivatives is of current interest because of its critical relationship to the mechanism of "borderline" solvolysis. l-4 Schleyer and his coworkers'
Selectivity in solvolysis of 1- and 2-adamantyl arenesulfonates and bromides in ethanol-2,2,2-trifluoroethanol
β Scribed by Takashi Ando; Shin-ichi Tsukamoto
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 237 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
## Abstract The rate constants (log __k__) for the solvolysis of 4^e^βsubstituted 2^e^β and 2^a^βadamantyl __p__βnitrobenzenesulfonates **14** and **15**, respectively, in 80% EtOH correlate linearly with the respective inductive substituent constants Ο. Therefore, relative rates are controlled by
Substituents at the remoter 5-position of 2-adamantyl arylsulfonates control solvolysis rates more strongly than substituents at the 4-position.
The title reaction has been studied with 2-methoxypropene, (E)-cyclooctene, ethoxyethene, 1,3-cyclopentadiene, 3methylenecyclohexene, styrene and isoprene as the olefinic substrates. This sequence is one of decreasing reactivity of the substrates towards 2-oxido-2-cyclopenten-1-ylium (1) if [4 + 3]
Aqueous micellar solutions containing cetyltrimethylammonium bromide (CTAB) and solubilized 2,2,2-trifluoro-1-( 9 -anthryl)-ethanol (TFAE) known to exhibit photorheological effects were investigated via (i) oscillatory shear viscometry, (ii) electrically induced birefringence, and (iii) dynamic ligh