39864-10-3Relevant articles and documents
Asymmetric synthesis of (R)-limonene and (S)-cembrene-A by an intramolecular cyclization reaction using a chiral leaving group
Ishihara,Nakamura,Yamamoto
, p. 1113 - 1116 (2001)
A six-membered monocyclic terpene, (R)-limonene, and a 14-membered monocyclic diterpene, (S)-cembrene-A, have been synthesized, respectively, by new enantioselective intramolecular cyclization reactions of neryl ether and (all-E)-geranylgeranyl ether using an (R)- 1,1′-binaphthyl-2-benzoxy-2′-oxy auxiliary as a chiral leaving group in the presence of tin(IV) chloride.
Bunton et al.
, p. 3238,3239-3241 (1979)
Allylic and allenic halide synthesis via NbCl5- and NbBr 5-mediated alkoxide rearrangements
Ravikumar,Yao, Lihua,Fleming, Fraser F.
supporting information; experimental part, p. 7294 - 7299 (2010/01/16)
(Chemical Equation Presented) Addition of NbCl5 or NbBr 5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metallahalo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared by nucleophilic addition, deprotonation, or reduction. Experimentally, the niobium pentahalide halogenations are rapid, afford essentially pure (E)-allylic or -allenic halides after extraction, and are applicable to a range of aliphatic and aromatic alcohols, aldehydes, and ketones. 2009 American Chemical Society.
Simple synthetic protocols for tertiary alkyl and allyl thiols
Gurudutt, K. N.,Rao, Sanjay,Srinivas, P.,Srinivas, S.
, p. 1169 - 1171 (2007/10/03)
Convenient preparative methods for tertiary alkyl and allyl thiols are described. Accordingly, thiolesters and thiocyanates, obtained from the reaction of SN1-active halides and appropriate zinc salts, on hydrolysis and LAH reduction respectively, afford the corresponding thiols in near quantitative yields. Besides the well known p-menth-1-ene-8-thiol, p-menthane-1-thiol, p-mentha-1,8-diene-6-thiol and 2-(2-phenyl)propane thiol have been prepared.