Regioselective photoamination of 4-nitroveratrole upon cyclodextrin complexation

Journal of Chemical Sciences

C Srinivasan1²  K Pitchumani¹  M C Durai Manickam² 

[1] School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India$$;Department of Materials Science, Madurai Kamaraj University, Madurai 625 021, India$$

关键词: Cyclodextrin;    4-nitroveratrole;    photoamination.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

Photoamination of 4-nitroveratrole in cyclodextrins with the nucleophiles ammonia, methylamine and hexylamine provides a new route to regioselectivity. This method gives a displaced product para to the nitro group as the predominant product, in contrast to the solution reaction wherein the meta-displaced product predominates. This is due to the change in the mechanistic shift from S𝑁2Ar∗, wherein the nitro group is meta-directing, to a mechanism involving electron transfer from the nucleophile to the excited aromatic substrate (S𝑁 (ET)Ar∗) to give the para-displaced product.

【 授权许可】

Unknown