Shin-etsu Chemical Co., Ltd.

Mitsuyoshi Oshima

Akira Yamamoto

Takehiko Fukumoto

Hiroshi Suzuki

Daisuke Iwai

Shigeo Okano

Toshinobu Ishihara

Masatoshi Arai

Hisashi Shimizu

Kenichi Taguchi

Ken'ichi Itoh

Nobuo Takasaka

Shigeru Saito

Disclosed are compounds suitable for use as raw materials which enable cis-olefin compounds useful as physiologically active substances such as the sex pheromones of various insects, or as intermediates for the synthesis thereof to be prepared on an industrial scale at a reasonable cost, and processes for the preparation of cis-olefin compounds by using the same. For this purpose, novel compounds (i.e., 1-halo-cis-3-tetradecenes) of the general formula (I)

1-Halo-cis-3-tetradecenes and processes for the preparation of

1-halo-cis-3-tetradecenes and processes for the preparation of

A refreshing agent comprising a compound having a hydrosilyl group and a hydrosilylation catalyst quickly adsorbs ethylene without forming hazardous substances and is thus suitable for keeping vegetables, fruits, and flowers fresh.

Refreshing agent

Disclosed is a novel ene-yne compound Z-12-heptadecen-1-yne expressed by the structural formula CH.sub.3 (CH.sub.2).sub.3 CH.sup.(Z) =CH(CH.sub.2).sub.9 C=CH, which is useful as an intermediate in the synthetic preparation of several diene compounds having activity as a sex pheromone of the insects belonging to the lepidopteran order, such as E,Z-2,13-octadecadienyl acetate and E,Z-2,13-octadecadienal, having two double bonds at the 2- and 13-positions. The inventive compound can be synthesized by the reaction of 1-bromo-Z-10-pentadecene with sodium acetylide dispersed in an organic solvent in the presence of liquid ammonia.

Z-12-heptadecen-1-yne

The invention provides a novel class of organic compounds 1-halo-4-decene as a useful intermediate for the synthesis of cis-6-heneicosen-11-one which is a promising exterminating chemical of the noxious insect Douglas-fir tussock moth in North American forests acting as a sexual pheromone. The synthetic procedures for the synthetic preparation of the above 1-halo-4-decene are also described.

1-Halo-4-decene compounds

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Joetsu, Japan

Mitsuyoshi Oshima