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Exploring the Reactivity of a Frustrated Sn/P Lewis Pair: The Highly Selective Complexation of the cis‐Azobenzene Photoisomer
- Source :
- Chemistry (Weinheim an Der Bergstrasse, Germany)
- Publication Year :
- 2021
- Publisher :
- John Wiley and Sons Inc., 2021.
-
Abstract
- The reactivity of the geminal frustrated Lewis pair (FLP) (F5C2)3SnCH2P(tBu)2 (1) was explored by reacting it with a variety of small molecules (PhOCN, PhNCS, PhCCH, tBuCCH, H3CC(O)CH=CH2, Ph[C(O)]2Ph, PhN=NPh and Me3SiCHN2), featuring polar or non‐polar multiple bonds and/or represent α,β‐unsaturated systems. While most adducts are formed readily, the binding of azobenzene requires UV‐induced photoisomerization, which results in the highly selective complexation of cis‐azobenzene. In the case of benzil, the reaction does not lead to the expected 1,2‐ or 1,4‐addition products, but to the non‐stereoselective (tBu)2PCH2‐transfer to a prochiral keto function of benzil. All adducts of 1 were characterised by means of multinuclear NMR spectroscopy, elemental analyses and X‐ray diffraction experiments.<br />A highly selective complexation of cis‐azobenzene was found when reacting the isomeric compound with the intramolecular frustrated Lewis pair (F5C2)3SnCH2P(tBu)2 under UV‐induced photoisomerization conditions.
- Subjects :
- Photoisomerization
010402 general chemistry
01 natural sciences
Medicinal chemistry
Catalysis
Frustrated Lewis pair
Adduct
chemistry.chemical_compound
tin
Reactivity (chemistry)
Geminal
Full Paper
010405 organic chemistry
Organic Chemistry
General Chemistry
Nuclear magnetic resonance spectroscopy
Full Papers
0104 chemical sciences
small molecules
chemistry
Azobenzene
fluoroalkyl groups
activation
Benzil
Frustrated Lewis Pairs | Hot Paper
frustrated Lewis pairs
Subjects
Details
- Language :
- English
- ISSN :
- 15213765 and 09476539
- Volume :
- 27
- Issue :
- 11
- Database :
- OpenAIRE
- Journal :
- Chemistry (Weinheim an Der Bergstrasse, Germany)
- Accession number :
- edsair.doi.dedup.....5c2ae69fb7b460f610f4e6bfb101877c