The reaction recently discovered leading to tetrahydropyrans (THP): has been more extensively investigated by using various allyltin systems, alternate incremental additions of two aldehydes, and scrambling organotin reagents. Unsymmetric halotetrahydropyrans containing various R groups can be readily prepared in this way. The thermal breakdown of the 12-dichloro adducts, namely (E/Z)1-alkyl-1-butyldichlorostannoxy, 1-alkyl-3-pentyl ethers and the (threo/erythro)-1-alkyl-1-butyldichlorostannoxy, 1-alkyl-2-methyl-3-butenyl ethers, is a stereospecific reaction which affords (E/Z)-halotetrahydropyrans, where the isomerism is at the CHClCH(CH3) bond

THE PREPARATION OF 4-CHLORO-2,6-DIALKYL-, 4-BROMO-2,6-DIALKYL-, (E/Z)-4-CHLORO-2,6-DIALKYL-3-METHYL-AND (E/Z)-4-BROMO-2,6-DIALKYL-3-METHYL-TETRAHYDROPYRANS BY CONDENSATION OF ALDEHYDES WITH DI-HALIDES AND TRI-HALIDES OF ALLYLTIN .9.

BOARETTO, ANDREA;FURLANI, DONATELLA;MARTON, DANIELE;TAGLIAVINI, GIUSEPPE;GAMBARO, ALESSANDRO
1986

Abstract

The reaction recently discovered leading to tetrahydropyrans (THP): has been more extensively investigated by using various allyltin systems, alternate incremental additions of two aldehydes, and scrambling organotin reagents. Unsymmetric halotetrahydropyrans containing various R groups can be readily prepared in this way. The thermal breakdown of the 12-dichloro adducts, namely (E/Z)1-alkyl-1-butyldichlorostannoxy, 1-alkyl-3-pentyl ethers and the (threo/erythro)-1-alkyl-1-butyldichlorostannoxy, 1-alkyl-2-methyl-3-butenyl ethers, is a stereospecific reaction which affords (E/Z)-halotetrahydropyrans, where the isomerism is at the CHClCH(CH3) bond
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11577/2489662
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