The conversion of 4-oxa-5-hexenyllithiums to 4-alken-1-ols: A novel [1,4]-wittig rearrangement

Article abstract of DOI:10.1016/0040-4039(91)80002-N

4-Oxa-5-hexenyllithiums (2), which may be prepared from the corresponding 3-iodoalkyl vinyl ethers (1) by low-temperature lithium - iodine exchange, rearrange in high yield to 4-alken-1-ols (4) when warmed to room temperature. This transformation, which constitutes a [1,4]-Wittig rearrangement, is mediated by 5-exo-trig closure of 2 to a (2-tetrahydrofuranyl)methyllithium (3) followed by spontaneous ring opening to give 4.