332367-86-9Relevant academic research and scientific papers
Synthesis and reactivity of allenes substituted by selenenyl groups at 1- and 3-positions
Shimizu,Miyasaka,Kamigata
, p. 1787 - 1794 (2007/10/03)
1,3-Bis(methylseleno)- and 1,3-bis(benzylseleno)-l,3-diphenylpropadienes were synthesized by reaction of Ph2C3 dianion, prepared from 1,3-diphenylpropyne and n-butyllithium, with dimethyl diselenide or benzylselenocyanate in the presence of TMEDA, and reaction of the dianion with a mixture of dimethyl diselenide and benzylselenocyanate yielded 1-benzylseleno-3-methylselenoallene along with the symmetric allenes. Diselenocyclic allenes and tetraselenocyclic bisallenes were also obtained by reacting the dianion with corresponding alkane diselenocyanates. The thermal reaction of the 1,3-bis(alkylseleno)allenes mainly afforded enediynes through radical pathway, and the nine-membered cyclic allene provided intramolecular cyclization product via an intramolecular rearrangement. Heating of the cyclic bisallenes gave compounds derived from intramolecular cyclization products together with a small amount of the enediynes. Irradiation of allenes caused rearrangement of the selenenyl group to give alkynes, and the alkynes also reacted photochemically to yield the enediynes.
