ChemInform Abstract: Reactions of Trialkyl(2‐furyl)germanes (I), (XII) with Electrophilic Reagents.

Lukevics, É.; Игнатович, Л.; Gol'dberg, Yu. Sh.; Polyak, F. D.; Gaukhman, A.; Rozīte, S.; Popelis, J.

doi:10.1002/chin.198849217

ChemInform

1988

DOI: 10.1002/chin.198849217

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ChemInform Abstract: Reactions of Trialkyl(2‐furyl)germanes (I), (XII) with Electrophilic Reagents.

É. Lukevics¹,

Л. Игнатович²,

Yu. Sh. Gol'dberg³

et al.

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1998

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“…If the reactions leading to ring contraction (pyran--furan) are more or less known then for ring expansion (furan--pyran) there are relatively few examples. Such reactions are observed if 2-methyl derivatives [8,9] are used as starting materials or there are present in the reaction medium components able to generate methyl radicals (the synthesis of tetrahydropyran from tetrahydrofuran over a ruthenium catalyst in the presence of CO and H2 is reported in [10]). …”

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Mutual catalytic conversions of unsubstituted furan and pyran systems

Anderson¹,

Simonyan²,

Lukevics³

1998

Chem Heterocycl Compd

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The conversions of furan, di-and tetrahydrofuran, and di-and tetrahydropyran on a molybdenum catalyst in a hydrogen atmosphere have been investigated. The studied cyclic systems readily undergo mutual conversions at 125-215"C and also undergo a hydrogenation-dehydrogenation reaction. Expansion of the unsubstituted furan rings to pyran without the introduction into the reaction medium of components capable of generating methyl radicals are described by us for the first time.The chemistry of the simplest oxygen containing five-[1, 2] and six-[1, 3] membered heterocyclic systems have been quite widely studied. These compounds find broad usage in fine organic synthesis and also (in particular tetrahydrofuran) in other branches of the chemical industry. Exceptions are the unsubstituted pyrans [4,5]; 4-H pyran being obtained only in 1962 [6,7] and 2H-pyran not obtained at all. The mutual interconversions of these heterocyclic systems have been quite inadequately studied. If the reactions leading to ring contraction (pyran--furan) are more or less known then for ring expansion (furan--pyran) there are relatively few examples. Such reactions are observed if 2-methyl derivatives [8,9] are used as starting materials or there are present in the reaction medium components able to generate methyl radicals (the synthesis of tetrahydropyran from tetrahydrofuran over a ruthenium catalyst in the presence of CO and H2 is reported in [10]).We have shown that five-and six-membered oxygen containing heterocycles are readily mutually interconverted without any other components in the reaction medium by passage over a molybdenum catalyst in a stream of hydrogen.The results of the conversion of furans and pyrans at 200~ are given in Table 1. As shown in the data obtained, the investigated 5-and 6-membered heterocycles are readily interconverted by reduction with the molybdenum catalyst; in all cases the reaction mixture contained all five compounds. There are also formed small amounts of low-molecular-weight decomposition products. The highest reactivity on the molybdenum catalyst is shown by furan and dihydrofuran and the lowest by tetrahydrofuran. The saturated heterocyclic

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confidence: 98%

Mutual catalytic conversions of unsubstituted furan and pyran systems

Anderson¹,

Simonyan²,

Lukevics³

1998

Chem Heterocycl Compd

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ChemInform Abstract: Reactions of Trialkyl(2‐furyl)germanes (I), (XII) with Electrophilic Reagents.

Cited by 1 publication

References 1 publication

Mutual catalytic conversions of unsubstituted furan and pyran systems

Mutual catalytic conversions of unsubstituted furan and pyran systems

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