Preparation of substituted cyclopentadienes

Details Preparation of substituted cyclopentadienes Preparation of substituted cyclopentadienes

1993-01-19

1994-07-12

Pal, Asok

Chemistry of hydrocarbon compounds

Alicyclic compound synthesis

From nonhydrocarbon

585357, C07C 120, C07C 1207

Patent

active

053290569

ABSTRACT:
A process is provided for preparing an substituted cyclopentadiene by the steps of (a) reacting a vinyl ketone with a vinyl organometallic compound to form a divinyl tertiary alcohol and (b) dehydrating/cyclizing the tertiary alcohol such as with an acid and/or heat to form the substituted cyclopentadiene.

REFERENCES:
patent: 4967033 (1990-10-01), Mahaim
Campbell et al: The Stereochemistry of Pentadienyl-Cyclopentadienyl Cation Rearrangement; Jour. Amer. Chem. Soc., vol. 91, pp. 6404-6410, 1969.
Gannan et al: 1,2,3,4-Tetralmethyl-5-(trifluoromethyl)-cyclopentadienide: A Unique Ligand With the Stereo-Properties of Pentamethyl Cyclopentadienide and the Electronic Properties of Cyclopentadienide, J. Amer. Chem. Soc., vol. 114, pp. 6942-6946, 1992.
Threlkel et al: 1,2,3,4,5-Pentamethylcyclopentadiene, Organic Synthesis, vol. 65, pp. 42-45, 1987.
Okamoto et al: Synthesis of Optically Active .gamma.-Trimethylsilyl-.beta.,.gamma.-epoxy Tertiary Alcohols by the Diastereoselective Addition Reaction of .beta.-Trimethylsilyl-.alpha.-.beta.-Epoxy Ketones with Grignard Reagents, Tetrahedron Letters, vol. 41, 1991, pp. S789-S792.
Weber et al: Enantiomerically Pure Tertiary Alcohols by TADDOL-Assisted Addition to Ketones-or How to Make a Grignard Reagent Enantioselective; Angew. Chim. vol. 31, 1992, pp. 84-86 (Int. Edition).
Journal of Organometallic Chemistry, 243 (1983) 119-121, "An Improved Synthesis of 1,2,3,4,5-Pentamethylcyclopentadiene", by Franz X. Kohl, et al.
Organometallics 1988, 7, 1828-1838, "Manipulation of Organoactinide Coordinative Unsaturation . . . " by Carol M. Fendrick, et al.

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