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Effect of Remote Substituents on the Torquoselectivity of 3‐Silyl Cyclobutene‐Derivatives Ring‐Opening Reactions
Author(s) -
Larrañaga Olatz,
Cózar Abel
Publication year - 2020
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202000451
Subject(s) - cyclobutene , chemistry , natural bond orbital , trimethylsilyl , silylation , substituent , density functional theory , steric effects , ring (chemistry) , reactivity (psychology) , computational chemistry , aryne , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
We have quantum chemically studied the structure and nature of 1‐substituted 3‐trimethylsilyl cyclobutenes and 2,2‐disubstituted‐7‐trimethylsilyl bycyclo[4.2.0]octa‐1(6),3‐dienes comparing their reactivity to archetypal 3‐substituted cyclobutene systems using density functional theory at M06‐2X(PCM)/TZ2P level. We wish to understand how the ring opening reaction is affected by a substituent not directly connected to the σ Carbon‐Carbon breaking bond. To this end, we have analyzed the reaction profiles considering second order perturbation energies and natural steric analysis within NBO framework.