The rearrangement of dihydropyran over alumina
Stouffer, John Emerson
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The mechanism of the unusual rearrangement ot tetrahydrofurfuryl alcohol over allumina at an elevated temperature to give good yield of dihydropyran has been ot considerable interest. It had previously been shown that the external methylene carbon of tetrahydrofurfuryl alcohol was found, after ring expansion had taken place, not only at the 2-position of delta2-dihydropyran as one might have expected, but in about half of the product at the 6 position instead. It then became quite important in terms ot eventual assignment ot a mechanism to this reaction, to determine if delta2-dihyydropyran, once formed, was itself capable of further rearrangement. The present research set out to establish whether or not this took place. [TRUNCATED]
Thesis (Ph.D.)—Boston University
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