Transmission of substituent effects in heterocyclic systems. The correlation and prediction of solvolysis rates for heteroarylmethyl derivatives.
✍ Scribed by Donald S. Noyce; Richard W. Nichols
- Publisher
- Elsevier Science
- Year
- 1972
- Tongue
- French
- Weight
- 213 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Recent studies indicate a renewed interest in the mode of interaction of substituents with reaction sites in heterocyclic systems. 3,4 We have investigated this question further through use of the solvolysis reaction: a very useful reaction in this respect, as it shows high sensitivity to resonance and field effects, and may be carried out on compounds of a wide range of reactivity under neutral conditions.
We wish to report notable success in dealing with the relative rates of solvolysis of a number of substituted heteroarylmethyl compounds, including a-heteroarylethyl E-nitrobenzoates of I-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, and 2-thienyl systems.
Bancroft and Howe' have shown that the Dewar-Grisdale equation6, when calibrated with Brown's7 0' constants rather than Hammett c constants gives greatly