THE SYNTHESIS OF 4-HALOTETRAHYDROPYRANS AND 4-HALO-5,6-DIHYDRO-2H-PYRANS VIA THE LEWIS ACID PROMOTED CYCLIZATION OF ACETALS OF HOMOALLYLIC AND HOMOPROPARGYLIC ALCOHOLS
Ethyl vinyl ether, MEM chloride, and dihydropyran based acetals of homoallylic and homopropargylic alcohols cyclize in the presence of Lewis acids to give 4-halotetrahydropyrans and 4-halo-5,6-dihydro-2H-pyrans, respectively.
Bunnelle, W. H.,Seamon, D. W.,Mohler, D. L.,Ball, T. F.,Thompson, D. W.
HIGH YIELD PREPARATION OF 2,3,3-TRICHLORINATED TETRAHYDROPYRAN WITH AN EXCESS OF REFLUXING SULFURYL CHLORIDE IN THE DARK
The chlorination of tetrahydropyran with an excess of refluxing sulfuryl chloride in the dark provided 2,3,3-trichlorotetrahydropyran in 94percent isolated yield, showing evidence for a very selective non-homolytic mechansims, probably involving hydride abstraction as the first step.
Buyck, Laurent de
p. 303 - 306
(2007/10/02)
Preparation of Cyclic Ethers via a Transacetalization-Cationic Cyclization Sequence
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Nikolic, Nikola A.,Gonda, Elizabeth,Longford, C. P. Desmond,Lane, Nancy T.,Thompson, David W.
p. 2748 - 2751
(2007/10/02)
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