109765-96-0Relevant academic research and scientific papers
Syntheis of 3-(1-Hydroxyalkyl)-5H-furan-2-ones: Study of their Reaction with Halogens
Calderon, Angel,March, Pedro de,Arrad, Mustafa el,Font, Josep
, p. 4201 - 4214 (1994)
The syntheis of 3-(1-hydroxyalkyl)-5H-furan-2-ones, 4a-c, is reported.The reaction of lactones 4a and 4b with bromine under typical ionic bromination conditions gives as major product the unexpected substitution of the allylic hydroxyl group.Only the less hindered double bond in 4c gives some proportion of the normal addition product.The bromine chloride addition to 4c proceeds with 55 percent yield, while lactone 4a does not add BrCl.All these results point to the fact that halogen addition to the double bond of 4 suffers at least from steric hindrance.Key words: 3-(1-hydroxyalkyl)-5H-furna-2-ones; bromination; bromine chlorination
Synthesis of 3-(1-Hydroxyalkyl)furan-2-(5H)-ones: Unexpected Substitution Reaction in Allylic Alcohols by Bromine
Calderon, A.,March, P. de,Font, J.
, p. 4631 - 4633 (2007/10/02)
Substitution of an allylic hydroxyl group on α,β-butenolide derivatives by bromine under typical ionic bromination conditions is reported.
