Rearrangements of (E,Z)-4-acetyl[17O]oxyhepta-2,5-diene catalysed by Pd0 and PdII: Mechanistic deductions from observations by 17O NMR spectroscopy
1984
Abstract ( E,Z )-4-Acetyl[ 17 O]oxyhepta-2,5-diene [MeCH E =CHCH( 17 OCOMe)CH Z =CHMe] has been synthesised and rearranged under Pd 0 - and Pd II -catalysis. The distribution of 17 O in the products of these rearrangements has been determined by 17 O NMR spectroscopy. With Pd 0 catalyst the product is a 1:1 mixture of MeCH E =CHCH E =CHCH( 17 OCOMe)Me and MeCH E =CHCH E =CHCH(OC 17 OMe)Me formed from an intermediate Pd-coordinated pentadienyl species and 17 O-acetate. With Pd II catalyst the product is MeCH Z =CHCH E =CHCH(OC 17 OMe)Me formed via an intermediate acetoxonium ion.
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