Uncatalysed addition reactions

Details Uncatalysed addition reactions Uncatalysed addition reactions

2005-03-15

2005-03-15

Price, Elvis O. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S816000, C568S817000, C568S819000, C568S731000, C568S732000, C568S734000, C568S743000, C568S825000

Reexamination Certificate

active

06867335

ABSTRACT:
The present invention relates to process wherein (+)-2-carene epoxide is coupled with a compound X—Y that contains nucleophilic and electrophilic moieties, to produce a compound of formula (5). The reaction mixture consists essentially of a source of (+)-2-carene epoxide, compound X—Y, optionally an inert solvent and optionally a pH buffer. No acid catalyst is used in the process.

REFERENCES:
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patent: 4025516 (1977-05-01), Razdan et al.
patent: 5227537 (1993-07-01), Stoss et al.
Aída L. Villa de P. et al., “Selective Epoxidation of Monoterpenes with Methyltrioxorhenium and H2O2,”Tetrahedron Letters, vol. 39, 1998, pp. 8521-8524.
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Benjamin C. Clark, Jr. et al., “Lewis Acid Rearrangement of 2,3-Epoxycarane. Formulation of a novelm-Menthenone,”J. Org. Chem., vol. 43, No. 3, pp. 519-520, 1982.
Kazushi Arata et al., “Isomerization of 2- and 3-Carene Oxides over Solid Acids and Bases,”J. Org. Chem., vol. 43, No. 9, 1978, pp. 1660-1664.
Raj K. Razdan et al., “Hashish. A Stereospecific Synthesis of (—)-Δ1-and (—)-Δ1(16)-Tetrahydrocannabinols,”Journal of the American Chemical Society, vol. 19, No. 20, Oct. 7, 1970, pp. 6061-6062.
International Search Report dated Sep. 12, 2002, from International Application No. PCT/GB02/02160.

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