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Understanding the Mechanism of S N 2′ vs . S N 2 in Cascade Reaction of β‐Naphthol and Nitrostyrene Derived MBH Acetates
Author(s) -
Kumar Vadiga Shanthi,
Gudise Veera Babu,
Settipalli Poorna Chandrasekhar,
Reddy Eeda Koti,
Firoj Basha Shaik,
Reddy Yeruva Pavankumar,
Srinivasadesikan V.,
Lee ShyiLong,
Anwar Shaik
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904618
Subject(s) - nitro , chemistry , electrophile , medicinal chemistry , base (topology) , cascade , minor (academic) , computational chemistry , stereochemistry , organic chemistry , catalysis , mathematical analysis , alkyl , mathematics , chromatography , political science , law
The reaction of β‐naphthol with nitrostyrene derived primary MBH acetates in presence of Cs 2 CO 3 as base resulted in the formation of 3‐nitro‐4‐phenyl‐3,4‐dihydro‐2H‐naphthopyran as the major isomer via S N 2′ process. Due to the bis‐electrophilic nature of MBH acetates, the minor product 3‐nitro‐2‐phenyl‐3,4‐dihydro‐2H‐naphthopyran was also obtained presumably due to S N 2 process with γ ‐attack on MBH acetates. The state of the art density functional theory (DFT) calculations were carried out to account for these competitive pathways towards the formation of major and minor products.