Intramolecular cyclization of nerol and the related attack of (Z)-allylic alcohol moiety on the terminal olefin linkage as induced by TiCl4-PhNHMe complex. Synthesis of …

A Itoh, T Saito, K Oshima, H Nozaki

Index: Itoh, Akira; Saito, Tadashi; Oshima, Koichiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 5 p. 1456 - 1459

Full Text: HTML

Citation Number: 18

Abstract

Nerol was cyclized to terpinyl chloride or bromide in the presence of TiX 4–PhNHMe (1: 1) complex (I, X= Cl, Br) in dichloromethane at− 23° C, geraniol being converted into geranyl halide by simple halogenation. Terminally modified derivatives YCH 2 C (Me)= CHCH 2 CH 2 CMe= CHCH 2 OH (Y= SiMe 3, SnBu 3) of (2Z, 6E) configuration were cyclized by treatment with I to afford limonene in high yields and 100% selectivity. Cyclization of (2Z) ...

Related Articles:

A novel reduction reaction for the conversion of aldehydes, ketones and primary, secondary and tertiary alcohols into their corresponding alkanes

[Nimmagadda, Rama D.; McRae, Christopher Tetrahedron Letters, 2006 , vol. 47, # 32 p. 5755 - 5758]

Highly regioselective diels-alder reactions of 2-trimethylsilylmethyl-1, 3-butadiene catalyzed by a lewis acid and applications to syntheses of terpenes

[Hosomi, Akira; Iguchi, Hirokazu; Sasaki, Jun-ichi; Sakurai, Hideki Tetrahedron Letters, 1982 , vol. 23, # 5 p. 551 - 554]

Fate of monoterpenes in near-critical water and supercritical alcohols assisted by microwave irradiation

[Organic and Biomolecular Chemistry, , vol. 8, # 7 p. 1560 - 1567]

Fate of monoterpenes in near-critical water and supercritical alcohols assisted by microwave irradiation

[Organic and Biomolecular Chemistry, , vol. 8, # 7 p. 1560 - 1567]

Fate of monoterpenes in near-critical water and supercritical alcohols assisted by microwave irradiation

[Organic and Biomolecular Chemistry, , vol. 8, # 7 p. 1560 - 1567]

More Articles...