PARTICIPATION IN THE FORMATION OF IODO UREAS FROM 3-BUTEN-1-OL DERIVATIVES. A REINVESTIGATION.

Article abstract of DOI:10.1016/S0040-4020(01)98853-2

Treatment of O-substitued derivatives of 3-buten-1-ol with silver cyanate and iodine, followed by ammonia, gave cyclic derivatives 5 and 6.These compounds were previously assigned the linear structures 3 and 4, respectively.Evidence in support of the proposed structural reassignment was obtained form high-field 1H and 13C NMR studies.Both 5 and 6 undergo loss of the ureido group upon treatment with water to give 9 and 10, and 12, respectively.Potential mechanism for the observed reactions are discussed.