29773-63-5Relevant academic research and scientific papers
Evidence for concerted processes in the course of the homoallenylic transposition
Aouf, Chahinez,Galy, Nicolas,Santelli, Maurice
, p. 3225 - 3233 (2013/04/24)
The hydrolysis of β-allenic tosylates produces mainly 2-methylenecyclobutanols resulting from a homoallenylic participation along with isomeric 2-methylenecyclobutanol minor products coming from a 1234-1243 rearrangement. Structures of various cyclopropylvinyl carbocations involved in the course of the hydrolysis have been determined by computational studies. For acyclic tosylates, the hydrolysis of one β-deuterated allenic tosylate confirmed the nucleophilic attack on the corresponding nonclassical carbonium ion before its evolution to a more stable cyclopropylvinyl carbocation. In the case of one cyclic β-allenic tosylate, the structure of the products has been checked by the use of deuterated isotopomer.
