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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 19, Number 6
JKCSEZ 19(6)
December 20, 1975 

The Reaction of Benzyl Arenesulfonate with N,N-Dimethylanilines (Ⅲ). Substituent Effects of Leaving Group for Benzyl Arenesulfonate

Benzyl Arenesulfonate와 N,N-디메틸아닐린과의 반응 (제3보). Benzyl Arenesulfonate의 난탈기의 치환기 효과
Soo-Dong Yoh

Benzyl arenesulfonate와 디메틸아닐린을 아세톤 중에서 35℃로 반응시켜 이탈기의 치환기효과를 연구한 결과 다음과 같은 결론을 얻었다. (1) 친핵시약이 피리딘에서 N,N-디메틸아닐린으로 바뀌어도 이탈기의 치환기효과는 변화가 없다. (2) p-MeO의 치환기정수는 아세톤에서 -0.35가 적당했다. (3) 치환 디메틸아닐린의 친핵력이 약할 수록 전이상태에서는 N에서 C로 전자이동이 보다 크며 C…O결합 개열은 보다 진행된 상태라고 생각된다.

Substituent effect of the leaving groups of the reaction of benzyl arenesulfonate with dimethylanilines in acetone at 35℃ was obtained with the following results. 1. Substituent effect of the leaving groups was not variable when changed from pyridine to N,N-dimethylaniline in nucleophile 2.In acetone, the Hammett σ constant of p-MeO of the leaving group was -0.35. 3. The weaker the nucleophilicity in dimethylaniline, the stronger the movement of electron from N to C, and the cleavage of the C…0 bond in transition state proceeds.

449 - 453
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