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Hetero Diels-Alder Reactions of Masked Dienes Containing Heavy Group 15 Elements
Authors: Kořenková Monika | Kremláček Vít | Hejda Martin | Turek Jan | Khudaverdyan Raffi | Erben Milan | Jambor Roman | Růžička Aleš | Dostál Libor
Year: 2020
Type of publication: článek v odborném periodiku
Name of source: Chemistry - A European Journal
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 1144 –1154
Titles:
Language Name Abstract Keywords
cze Diels-Alder Reakce jednomocných sloučenin Dienové komplexy byly studovány v 2 2 cykloadicích jednomocných sloučenin Diels-Alder reakce; jednomocné sloučeniny
eng Hetero Diels-Alder Reactions of Masked Dienes Containing Heavy Group 15 Elements Treatment of N,C,N-chelated organopnictogen(I) compounds ArE (1-3) (Ar=2,6-(RN=CH)(2)C6H3, E/R=As/Dmp (1), Sb/tBu (2), and Bi/tBu (3), where Dmp=2,6-Me2C6H3) with various electron-deficient alkynes RC equivalent to CR ' (R/R '=CO2Me (DMAD), R/R '=H/CO2Me, or R/R '=NC5F4) affords different types of heterocyclic compounds. In these reactions, 1-3 act as hidden dienes and participate in hetero-Diels-Alder (DA) reactions, a feature that has been only rarely reported for heavier pnictogen compounds. In this way, reactions of 1 furnished the set of 1-arsanaphthalenes 4-6. The most likely mechanism involves two steps, that is, an arsa-DA reaction giving a 1-arsa-1,4-dihydro-iminonaphthalene, followed by CH -> NH proton migration. In contrast, this reaction sequence terminates at the first step in the case of the antimony analogue 2, thus giving the 1-stiba-1,4-dihydro-iminonaphthalenes 7 and 8. Reactions of the bismuth congener 3 gave one of two products depending on the alkyne used. Reaction of 3 with DMAD gave 1-bisma-1,4-dihydro-iminonaphthalene 9, whilst its reaction with two equivalents of HC equivalent to C(CO2Me) gave bismacyclohexadiene (10). All compounds have been characterized by NMR, IR, and Raman spectroscopies and X-ray diffraction analysis. The experimental data were complemented by a computational study, including a description of the reaction profiles of the hetero-DA reactions and an assessment of the aromaticities of the heterocyclic naphthalene derivatives. Diels-Alder reaction; heterocycles; heterodienes; heteronaphthalenes; pnictogens

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