Tetrahedron

Syntheses of bicyclic 1, 2-diols via the ring-expansion of bridgehead aldehydes of bicyclo [3.2. 1] octane and bicyclononanes with benzoyl triflate

K Takeuchi, K Ikai, M Yoshida, A Tsugeno

Index: Takeuchi, Ken'Ichi; Ikai, Keizo; Yoshida, Masayasu; Tsugeno, Akio Tetrahedron, 1988 , vol. 44, # 18 p. 5681 - 5694

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Citation Number: 14

Abstract

Bridgehead aldehydes of bicyclo [3.2.] loctane (11a), bicycio-[3.3. 1] nonane (12a), and bicyclo [3.2. 2] nonane (13a) have been subjected toacylative ring-expansion by using benzoyl trifluoromethanesulfonate (trif-late) to give mixtures of two or three bicyclic 1, 2-diol monobenzoates containing the hydroxyl group on the bridgehead carbon. Control experiments have shown that the reaction is kinetically controlled. The direction of the ring ...