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Asymmetric Epoxidation Of Dihydronaphthalene With A Synthesized Jacobs

2850 words - 12 pages

Asymmetric Epoxidation of Dihydronaphthalene with a Synthesized Jacobsen's

Abstract. 1,2 diaminocyclohexane was reacted with L-(+)-tartaric acid to yield
(R,R)-1,2-diaminocyclohexane mono-(+)-tartrate salt. The tartrate salt was then
reacted with potassium carbonate and 3,5-di-tert-butylsalicylaldehyde to yield
(R,R)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, which was
then reacted with Mn(OAc)2*4H2O and LiCl to form Jacobsen's catalyst. The
synthesized Jacobsen's catalyst was used to catalyze the epoxidation of
dihydronaphthalene. The products of this reaction were isolated, and it was
found that the product yielded 1,2-epoxydihydronaphthalene ...view middle of the document...

Experimental Section

     General Protocol. 99% L-(+)- Tartaric Acid, ethanol,
dihydronaphthalene and glacial acetic acid were obtained from the Aldrich
Chemical Company. 1,2 diaminocyclohexane (98% mix of cis/trans isomers) and
heptane were obtained from the Acros Chemical Company. Dichloromethane and
potassium carbonate were obtained from the EM Science division of EM Industries,
Inc. Manganese acetate was obtained from the Matheson, Coleman and Bell
Manufacturing Chemists. Lithium chloride was obtained form the JT Baker
Chemical Co. Refluxes were carried out using a 100 V heating mantle (Glas-Col
Apparatus Co. 100 mL, 90 V) and 130 V Variac (General Radio Company). Vacuum
filtrations were performed using a Cole Parmer Instrument Co. Model 7049-00
aspirator pump with a Büchner funnel. For Thin Layer Chromatography (TLC)
analysis, precoated Kodak chromatogram sheets (silica gel 13181 with
fluorescent indicator) were used in an ethyl acetate/hexane (1:4) eluent.
TLC's were visualized using a UVP Inc. Model UVG-11 Mineralight Lamp (Short-wave
UV-254 nm, 15 V, 60 Hz, 0.16 A). Masses were taken on a Mettler AE 100. Rotary
evaporations were performed on a Büchi Rotovapor-R. Melting points were
determined using a Mel-Temp (Laboratory Devices, USA) equipped with a Fluke 51
digital thermometer (John Fluke Manufacturing Company, Inc.). Optical rotations
([a]D) were measured on a Dr. Steeg and Renter 6mbH, Engel/VTG 10 polarimeter.
Solid IR's were run on a Bio-Rad (DigiLab Division) Model FTS-7 (KBr:Sample
10:1, Res. 8 cm-1, 16 scans standard method, 500cm-1 - 4000cm-1). Flash
Chromatography was carried out in a 20 mm column with an eluant of ethyl acetate
(25%) in hexane.

     (R,R)-1,2 Diaminocyclohexane mono-(+)-tartrate salt. 99% L-(+)-Tartaric
Acid (7.53g, 0.051mol) was added in one portion to a 150 mL beaker equipped
with distilled H2O (25 mL) magnetic stir bar, and thermometer. Once the
temperature had dropped to 17.8 °C, 1,2 diaminocyclohexane (11.89 g, 12.5 mL,
0.104 mol) was added with stirring in one portion. To the resultant amber
solution was added glacial acetic acid (5.0 mL, 0.057 mol). The frothy orange
product was cooled in an ice water bath for 30 minutes. The product was washed
with 5 °C distilled H2O (5.0 mL) and ambient temperature methanol (5.0 mL) and
isolated by vacuum filtration. 8.37 grams of an orange slush were obtained.
The product was further purified by recrystallization of the salt from H2O (1:10
w/v, 84 mL of H2O) and again isolated by vacuum filtration, yielding an off-
white crystalline product (1.2015g; 0.00415 mol; 8.9 % yield; mp=270.4-273.8 °
C Lit. Value mp=273 °C )

     (R,R)-N,N'-Bis (3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine.
Distilled H2O (6.0 mL), (R,R)-1,2 diaminocyclohexane mono-(+)-tartrate salt
(1.1087 g, 0.0042 mol) and K2CO3 granules (1.16 g, 0.0084 mol) were added to a

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