83867-60-1Relevant academic research and scientific papers
Regioselective Ene-Type Allylic Chlorination of Electron-Rich Alkenes by Activated DMSO
Demertzidou, Vera P.,Pappa, Stavroula,Sarli, Vasiliki,Zografos, Alexandros L.
, p. 8710 - 8715 (2017)
A simple protocol involving the activation of DMSO by chlorotrimethysilane is described for the chemoselective chlorination of polyprenoids. The proposed protocol provides a versatile and scalable alternative to existing routes for accessing useful synthe
FACILE FRAGMENTATION OF PINENES USING DIMETHYL SULFOXIDE ACTIVATED BY PHENYL DICHLOROPHOSPHATE OR PHOSPHORUS OXYCHLORIDE. EFFICIENT CONVERSION OF α-PINENE TO CARVONE
Liu, Hsing-Jang,Nyangulu, James M.
, p. 5097 - 5098 (2007/10/02)
Treatment of pinenes with dimethyl sulfoxide in the presence of phenyl dichlorophosphate or phosphorus oxychloride resulted in facile fragmentation giving rise to limonene derivatives.The fragmentation reaction serves as a key step in the efficient conversion of α-pinene (1) to carvone (7).
Reactions of d-Limonene with t-Butyl Hypochlorite
Ravindranath, B.,Srinivas, P.
, p. 163 - 165 (2007/10/02)
Investigation of the title reaction under different conditions of temperature, solvents and catalysis has led to its optimisation with respect to the yield of (-)-trans-carvyl chloride (2).Other products formed in the reaction have been identified as 1,2-dichloro-p-menth-8-ene (5), 10-chloro-p-mentha-1,8-diene (6), 2-chloro-p-mentha-1(7)8-diene (10) and 6,10-dichloro-p-mentha-1,8-diene (11).The reaction proceeds almost entirely by electrophilic halogenation with no evidence of competition from a radical mechanism.
Some Novel Esters of Carveol
Ravindranath, B.,Srinivas, P.
, p. 666 - 667 (2007/10/02)
Reaction of limonene (1) with t-butyl hypochlorite yields carvyl chloride as the major product, which is readily converted into carvyl acetate, carveol and carvone.Several novel esters of carveol, namely cis and trans carvyl benzoate, cinnamate, phenoxyacetate and phenylacetate have also been prepared for the first time in a one-pot reaction of carvyl chloride with the corresponding zinc carboxylate.
REACTION OF CIS-CARVEOL WITH TRIPHENYLPHOSPHINE AND TETRACHLOROMETHANE: A NOTE ON THE MECHANISM OF THE LEE REACTION
Ravindranath, B.,Srinivas, P.
, p. 3991 - 3994 (2007/10/02)
The title reaction yielded trans-carvyl chloride 2 and pinol 3.The formation of pinol and the specific rotation of the carvyl chloride are affected by the presence of acid.The implications of these findings on the understanding of the course of he reaction are discussed.Use of an acid scavenger is recommended in application of the PPh3-CCl4 reagent for acid sensitive compounds.A bimolecular, concerted group transfer mechanism (Scheme 2) is suggested for the decomposition of the intermediate alkoxytriphenylphosphonium halide 7.
