On treatment with Pd(PPh(3))(4) allyl vinyl ether (1) undergoes a Pd(0
) catalysed 1,3 oxygen to carbon allyl shift to afford alpha-allyl ket
one (2). In the presence of both Pd(PPh(3))(4) and base the allyl viny
l ether undergoes a Pd(0) catalysed tandem 1,3 allyl shift and intramo
lecular Heck arylation to give the spiro indane (3). Mechanistic inves
tigations suggest that the 1,3-allyl shift proceeds via a pi-allyl pal
ladium intermediate.