514853-82-8Relevant academic research and scientific papers
A direct route to conjugated enediynes from dipropargylic sulfones by a modified one-flask Ramberg-Baecklund reaction
Cao, Xiaoping,Yang, Yuying,Wang, Xiaolong
, p. 2485 - 2489 (2002)
The reaction of dipropargylic sulfones with dibromodifluoromethane in the presence of alumina-supported KOH in dichloromethane solution results in facile rearrangement affording the corresponding conjugated linear and cyclic enediynes in good yields. This result shows that the direct transformation of a- and a′-hydrogen bearing sulfones assembles enediyne units without resorting to the prior preparation of the a-halo sulfone precursors in a separate step.
Oxygen-Tethered 1,6-Enynes and [41.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry
Laher, Romain,Gentilini, Emilie,Marin, Christophe,Michelet, Véronique
, p. 4020 - 4029 (2021/08/10)
The synthesis of original structures for the fragrance industry bearing bicyclic scaffolds is described. To the best of our knowledge, these structures are not found in the fragrance industry, neither from natural nor synthetic pathways. NHC-gold-type catalysts showed excellent activities leading to light bicyclic enol ethers. Several bicyclic adducts were prepared in good to excellent yields (18-99%). Evaluation of NHC-Au complexes allowed to reach a TOF of 300 h -1. The evaluation for the organoleptic properties of [4.1.0]-bicyclic ethers were compared with the unprecedented properties of the 1,6-enyne precursors. Evaluations of starting materials showed a great interest in these structures with various olfactory facets. In this study, we depicted the similarity and differences between starting ethers and their cycloisomerized bicyclic counterparts.
Synthesis and reactivity of dipropargylic disulfides: tandem rearrangements, cyclization, and oxidative dimerization
Braverman, Samuel,Cherkinsky, Marina,Meridor, David,Sprecher, Milon
scheme or table, p. 1925 - 1930 (2010/04/24)
Synthesis and facile rearrangement and cyclization reaction of new dipropargylic disulfides are described. A possible mechanism for these transformations involving an initial double [2,3]-sigmatropic rearrangement to the elusive diallenyl disulfides via a thiosulfoxide intermediates is suggested.
Direct conversion of dipropargylic sulfones into (E)- and (Z)-Hex-3-ene-1,5-diynes by a modified one-flask Ramberg-Backlund reaction
Cao,Chan,Chow
, p. 1049 - 1052 (2007/10/03)
(E)- and (Z)-enediynes 7 are readily synthesized in good yields from a one-pot modified Ramberg-Backlund reaction from dipropargylic sulfones 5.
