Tetrahedron p. 1647 - 1656 (1982)
Update date:2022-07-31
Topics:
Thies, H.
Wolfschuetz, R.
Frenking, G.
Schmidt, J.
Schwarz, H.
The gas phase proton catalysed water elimination of tetrahydrofurfuryl alcohol (1) gives exclusively the ring-enlarged oxonium-ion 12.There is no experimental indication for the generation of 11 via a <1.2>-hydrogen migration.From the analysis of appropriately 13C-labelled precursors in combination with collisional activation mass spectrometry the mechanism for the ring-enlargement has been derived, clearly indicating that the oxygen/carbon bond is cleaved.A comparison of the experimental results with computational investigation (ab initio molecular orbital calculations at the 4-31G level) suggests that free tetrahydrofurfuryl cation 7 is not generated in the gas phase solvolysis.The elimination of H2O from the protonated molecule of 1 is a process characterised by anchimeric assistance of the ether oxygen 15.
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Doi:10.1002/anie.200351884
(2003)Doi:10.1021/acs.orglett.8b03303
(2018)Doi:10.1021/ja01296a005
(1936)Doi:10.1021/ja00388a091
(1982)Doi:10.1021/jo00147a002
(1982)Doi:10.1016/S0040-4039(00)81948-6
(1983)
