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Nonplanar phenyl ring and inverse order of solvolytic reactivity for tertiary benzylic substrates (1988)

Liu, Kwang-Ting ; Kuo, Mann-Yan ; Wang, Yu

Chichester : Wiley-Blackwell

Journal of Physical Organic Chemistry 1 (1988), S. 241-245

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ISSN: 0894-3230

Keywords: Organic Chemistry ; Physical Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology , Physics

Notes: The rates of solvolysis of l-aryl-l-phenyl-2,2-dimethylpropyl(1) p-nitrobenzoates and of aryldiphenylmethyl-p-nitrobenzoates (2) were measured in 80% acetone. An inverse order of reactivity, kp-CF3/km- CF3 〉 l was observed for 1 but not for 2. The X-ray crystallogoraphic study of the parent compounds, l,l-diphenyl-2,2-dimethylpropyl-p-nitrobenzoate (1b) and triphenylemethyl benzoate (3b), and of 2-phenyl-2-propyl-p-nitrobenzoate (4) indicated that in the highly congested system 1 both phenyl rings were nonplanar, whereas the phenyl rings in 3 and 4 were essentially planar.

Additional Material: 4 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/poc.610010407

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