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Keywords:

  • 1,2-addition;
  • 1,4-addition;
  • esters;
  • frustrated Lewis pairs;
  • ketones

Abstract

The frustrated Lewis pair (FLP) Mes2PCH2CH2B(C6F5)2 (1) reacts with an enolizable conjugated ynone by 1,4-addition involving enolate tautomerization to give an eight-membered zwitterionic heterocycle. The conjugated endione PhCO-CH[DOUBLE BOND]CH-COPh reacts with the intermolecular FLP tBu3P/B(C6F5)3 by a simple 1,4-addition to an enone subunit. The same substrate undergoes a more complex reaction with the FLP 1 that involves internal acetal formation to give a heterobicyclic zwitterionic product. FLP 1 reacts with dimethyl maleate by selective overall addition to the C[DOUBLE BOND]C double bond to give a six-membered heterocycle. It adds analogously to the triple bond of an acetylenic ester to give a similarly structured six-membered heterocycle. The intermolecular FLP P(o-tolyl)3/B(C6F5)3 reacts analogously with acetylenic ester by trans-addition to the carbon–carbon triple bond. An excess of the intermolecular FLP tBu3P/B(C6F5)3, which contains a more nucleophilic phosphane, reacts differently with acetylenic ester examples, namely by O[BOND]C(alkyl) bond cleavage to give the {R-CO2[B(C6F5)3]2}[alkyl-PtBu3+] salts. Simple aryl or alkyl esters react analogously by using the borane-stabilized carboxylates as good leaving groups. All essential products were characterized by X-ray diffraction.

Featured Compounds

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  1. 1 - 27
Compound 1
Molecular Weight:642.318
Molecular Formula:C32H26BF10P
InChIKey:BTBZHMNMVXKTII-UHFFFAOYSA-N
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Compound 2
Molecular Weight:761.438
Molecular Formula:C39H31BF10NOP
InChIKey:AAVBLIYMANBPNS-DMRQBMQDSA-N
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Compound 4
Molecular Weight:748.44
Molecular Formula:C39H32BF10OP
InChIKey:QRPQDWUVPLQKMZ-UHFFFAOYSA-N
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Compound 5
Molecular Weight:774.477
Molecular Formula:C41H34BF10OP
InChIKey:NKGBSRSCYJPHRP-OUKQBFOZSA-N
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Compound 3
Molecular Weight:686.327
Molecular Formula:C33H26BF10O2P
InChIKey:IEBURECTGDJQHG-UHFFFAOYSA-N
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Compound 6
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:LTAPKZGQTMVYMX-UHFFFAOYSA-N
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Compound 8
Molecular Weight:752.471
Molecular Formula:C39H36BF10OP
InChIKey:NGLHJVZGGOYLBK-BZZOAKBMSA-N
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Compound 9
Molecular Weight:236.2653
Molecular Formula:C16H12O2
InChIKey:WYCXGQSQHAXLPK-VAWYXSNFSA-N
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Compound 10a
Molecular Weight:714.296
Molecular Formula:C30H27BF15P
InChIKey:GHGCDMVTIQGJAJ-UHFFFAOYSA-N
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Compound 11
Molecular Weight:950.561
Molecular Formula:C46H39BF15O2P
InChIKey:UVIBKEMNPFKBRT-ATJXCDBQSA-N
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Compound 13
Molecular Weight:878.583
Molecular Formula:C48H38BF10O2P
InChIKey:FLQMDDXLSSQRBB-TYIFYYBUSA-N
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Compound 15
Molecular Weight:786.443
Molecular Formula:C38H34BF10O4P
InChIKey:GQZUUPZKEOCJDA-MBXDFBHOSA-N
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Compound 16a
Molecular Weight:98.0999
Molecular Formula:C5H6O2
InChIKey:UJQCANQILFWSDJ-UHFFFAOYSA-N
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Compound 16b
Molecular Weight:98.0999
Molecular Formula:C5H6O2
InChIKey:FMVJYQGSRWVMQV-UHFFFAOYSA-N
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Compound 10b
Molecular Weight:816.345
Molecular Formula:C39H21BF15P
InChIKey:YTWOQYOWVZRECA-UHFFFAOYSA-N
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Compound 18
Molecular Weight:740.418
Molecular Formula:C37H32BF10O2P
InChIKey:YECVCTNTLARRNK-UHFFFAOYSA-N
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 19
Molecular Weight:914.445
Molecular Formula:C44H27BF15O2P
InChIKey:SENOXJMRWSZCMV-RELWKKBWSA-N
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Compound 20
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21a
Molecular Weight:1324.376
Molecular Formula:C53H33B2F30O2P
InChIKey:ANTSXLCGKGPDDH-UHFFFAOYSA-N
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Compound 21c
Molecular Weight:1400.472
Molecular Formula:C59H37B2F30O2P
InChIKey:MIYHVLPURRYMDC-UHFFFAOYSA-N
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Compound 22a
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:WDAXFOBOLVPGLV-UHFFFAOYSA-N
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Compound 22b
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:MTZQAGJQAFMTAQ-UHFFFAOYSA-N
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 23a
Molecular Weight:1342.434
Molecular Formula:C54H39B2F30O2P
InChIKey:BVBPVLZZPHZYJM-UHFFFAOYSA-N
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Compound 23b
Molecular Weight:1376.45
Molecular Formula:C57H37B2F30O2P
InChIKey:FDHJJQFJNQNMFC-UHFFFAOYSA-N
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  1. 1 - 27