On the Dehydrating Isomerization of Linalool with Boron Trifluoride or Iodine

Abstract

The reaction of linalool (1) with boron trifluoride er iodine has been reexamined, since the formations of B-pinene (3) were claimed in these reactions by several authors.
In the case of boron trifluoride, the dehydration of (Z) afforded B-myrcene and then Bmyrcene was isomerized partly to limonene. Thislimonene was further isomerized to aterpinene and isoterpinolene, and a formation of P-cymene occurred due to the disproportionation accompanying by a formationof p-menthane. Dehydromyrcene and many other CieHis F2 0r CieHi6Fg compounds were also formed simultaneously.
The more complex reactions occured in the case of iodine.
In every case, a formation of (3), a-pinene or camphene was never observed.
The results are shown in Table 1 and 2.