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Intramolecular CH‐Hydrogen Bonding During the Dissociation of the Oxaphosphetane Intermediate Facilitates Z/E‐Selectivity in Wittig Olefination.
- Source :
- ChemistryOpen; Mar2024, Vol. 13 Issue 3, p1-9, 9p
- Publication Year :
- 2024
-
Abstract
- Herein, DFT studies corroborating experimental results revealed that the shortest intramolecular hydrogen bonding distance of cis/trans‐oxaphosphetane (OPA) oxygen with the CH‐hydrogen of a triphenylphosphine phenyl ring provides good evidence for the attained olefin Z/E‐selectivity in Wittig olefination of the studied examples. 2‐Nitrobenzaldehyde, 3‐nitrobenzaldehyde, 2‐nitro‐3‐bromobenzaldehyde, 2‐nitro‐5‐bromobenzaldehyde and 2‐nitro‐5‐arylbenzaldehydes provided Z‐nitrostilbenes with (2‐chloro‐4‐hydroxy‐3‐methoxy‐5‐(methoxycarbonyl)benzyl) triphenylphosphonium chloride as the major products. However, 4‐nitrobenzaldehyde and 2‐nitro‐6‐bromobenzaldehydes furnished E‐nitrostilbenes as the major products in high yields. Furthermore, the DFT computed intramolecular CH1/CH2‐hydrogen bond distances with Cl/NO2 of selected stilbene derivatives were in good agreement with intramolecular hydrogen bond distances measured from single‐crystal X‐ray diffraction measurements. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 21911363
- Volume :
- 13
- Issue :
- 3
- Database :
- Complementary Index
- Journal :
- ChemistryOpen
- Publication Type :
- Academic Journal
- Accession number :
- 175945563
- Full Text :
- https://doi.org/10.1002/open.202300171