Cyril A. Grob (1917–2003): Fragmentation and Inductivity
✍ Scribed by Peter Schiess
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 47 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0044-8249
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📜 SIMILAR VOLUMES
The effects of substituents at C5, C6 and C7 on the solvolysis rates of 2-norbornyl p-toluene sulfonates confirm that through space induction is directional and depends on distance and bridging strain.
As derived from the Hammetr equation log k/ko = pI 'cr ? where k and ko are rate constants for substituted and unsubstituted tosylates, respectively, and u? are inductive substituent constants [2]. The p , values for C(1) in 3 and 4 are presented and discussed in this communication. The dotted lines
Inductivity was defined as thc reaction constant p, in the equation log (klk,) = pluq, where k and k, are fmt-order rate consmiits for the substitutcd and unsubstituted tosylates, respectively, in 80% EtOH and u? i s the corresponding inductive substituent constant [3]. For recent reviews, see [2].
## Abstract α‐Methylthio‐propiophenone __anti__‐oxime __p__‐toluenesulfonate (tosylate) (**12b**) fragments quantitatively in 80% ethanol yielding benzonitrile and a methylidenesulfonium ion **15**. The __syn__‐isomer, however, undergoes a __Beckmann__ rearrangement. The fragmentation of α‐methylth