Neryl chloride

Three reaction sequences, all of a similar nature, have been published by Fujita and coworkers. The first175 is an alkene synthesis in which only three examples that involve sulphones are given. The most useful of these is a conversion of nerly phenyl sulphone (from neryl chloride) into aCn triene (75%), with the extra carbon atom being supplied by the iodomethylstannane reagent. The reaction proceeds spontaneously, with apparent retention of configuration at the Z alkene, as in equation (72). 

In addition, 85-90% yields of neryl chloride could be obtained from nerol, the geometrical isomer of geraniol. A modification4 of the above method has appeared which employs methanesulfonyl chloride and a mixture of lithium chloride, dimethylformamide, and collidine at 0° however, its applicability to compounds possessing sensitive groups was not demonstrated. 

NEOPENTYL IODIDE, 51, 44 Nerol, 54, 70 Neryl chloride, 54, 70 Nickel carbonyl, precautions for handling, 52, 117 reaction with allyl halides,... 

Isoprene reacts with dimethylallyl chloride in the presence of CuC1-A1203 to yield geranyl chloride, neryl chloride, lavandulyl chloride, and myrcene(12) 111 reaction of (39 X = C1) with antimony trichloride gives (E)- and (Z)-2,6-dimethylocta-2,5,7-trien-4-one.111 (E)- and (Z)-3,7-Dimethylocta-3,6-dien-l-ols, geraniol (8), nerol (18), and the dienol (40) are prepared from isopentenyl acetate and prenyl chloride... 

Geranyl-neryl chloride Linalyl chloride Scheme 4.2... 

Aside from the stoichiometric construction of steroidal side chains by the reaction of alkenylzirconium derivatives with steroidal 7r-allylpalladiums, a one-pot synthesis of a-famesene and its 6Z-isomer from generanyl and neryl chlorides, respectively, reported in 1981 appears to be the first example of natural product syntheses via Pd-catalyzed allylation (Scheme 21). 

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