Novel halo-oxo-allenic fatty ester derivatives from epoxidized methyl santalbate (methyl trans-11-octadecen-9-ynoate)

Electrophilic Cyclizations of 2‐Fluoroalk‐3‐yn‐1‐ones: Room‐Temperature Synthesis of Diversely 2,5‐Disubstituted 3,4‐Fluorohalofurans

“…[ 24] We focused our attention on N-halosuccimides, halogenating reagents superior to elemental halogen regarding its convenient handling and efficiency of halogen use. Engagement of the carbonyl oxygen atom in N-halosuccimide in interactions with Brønsted or Lewis acids may enhance dissociation into electrophilic halogen and thus increase the halogenating ability.…”

Expanding the Field of Phosphorus‐Containing Fatty Acid Derivatives: Synthesis of 1,2‐Oxaphospholene Derivatives and Alkenyl Phosphonates from α‐Keto Allenes

“…[6] Methyl santalbate [methyl (E)-octadec-11-en-9-ynoate from Sandalwood seed oil, Santalum album] was converted in a multistep reaction into methyl 11-chloro-12-oxo-9,10-octadecadienoate (2). [7] The α-chloro-αЈ-keto allene 3 was obtained by FriedelϪCrafts acylation of methyl santalbate. [8] According to the work of Buono et al [5] we reacted compound 1 with one equivalent of previously distilled trimethyl phosphite in dichloromethane by stirring at room temperature for 43 h (Scheme 2).…”

Introduction of Halogen Atoms into Organic Compounds Under Solvent- Free Reaction Conditions

“…of KHF 2 ) [39,40], while lower regioselectivity of the transformation was established and two anti products were formed (F20e1, F20e2). Bu 4 NH 2 F 3 as a source of fluoride anion has been successfully applied for the fluorofunctionalisation of various bioactive compounds among the epoxides (F21, Scheme F6) [36,[41][42][43]. Nitrogen atom was replaced by phosphorus in the cationic part of fluorides and the important role of the content of fluoride in the reagent on reactivity and regioselectivity was found.…”