Selective dealkylations of aryl alkyl ethers and thioethers by sodium in HMPA

…, M Tiecco, M Tingoli, D Chianelli, M Montanucci

Index: Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D.; Montanucci, M. Tetrahedron, 1982 , vol. 38, # 24 p. 3687 - 3692

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Citation Number: 36

Abstract

The reaction of sodium with bis-and tris (alkoxy) benzenes in HMPA gives selectively the products of monodealkylation. The reaction proceeds through a dianion which fragments into an alkyl and an aryloxy anion. The positional selectivity of this fragmentation is governed by the structure of both the alkyl and aryloxy groups. With bis-and tris (alkoxy) benzenes which for symmetry reasons can afford aryloxy anions having the same basicity, ...