2-dimethylphosphanylethyl(dimethyl)phosphane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (C6H5)2PCH2CH2P(C6H5)2 ; (CH3CH2)2PCH2CH2P(CH2CH3)2 ; (CH3)2PCH2CH2P(CH3)2; (C6H5)2PCH2P(C6H5)2 ; and [(C6H5)2PCH2CH2 ]2P(C6H5).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (C6H5)2PCH2CH2P(C6H5)2 ; (CH3CH2)2PCH2CH2P(CH2CH3)2 ; (CH3)2PCH2CH2P(CH3)2; (C6H5)2PCH2P(C6H5)2 ; and [(C6H5)2PCH2CH2 ]2P(C6H5).

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an atmosphere of dry nitrogen, 103 mg 1,5-cyclooctadiene(H5-indenyl)iridium (I) was put in a 25 mL Pyrex bottle. Subsequently were added 0.04 mL 1,2-bis(dimethylphosphino)ethane, 0.61 mL 3-bromochlorobenzene and 1.52 mL pinacolborane. The mixture was stirred at 150° C. for 3.5 h. After cooling to room temperature, the borane adduct was taken up in 17 mL acetone to give a clear solution. This solution was added slowly to 17.41 mL of a 0.30 M solution of oxone in water cooled in an ice bath. The mixture was stirred vigorously for 15 min. at room temperature and extracted three times with DCM. The combined organic phases were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM) to yield 750 mg (62%) of a beige solid. 1H NMR complies with known data (compound (I), Maleczka, 2003). After cooling to room temperature to give a clear solution cooled in an ice bath The mixture was stirred vigorously for 15 min. at room temperature extracted three times with DCM The combined organic phases were dried over Na2SO4 evaporated to dryness The residue was purified by flash chromatography (DCM)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepare a saturated solution of sodium chloride in ethanol by dissolving 117 mg of sodium chloride in 20 ml of degassed ethanol. Add 11.1 μl of liquid DMPE to this solution and adjust its pH to approximately 2.25 by adding concentrated hydrochloric acid. Dispense 5 ml into a 10 cc vial and crimp seal it using a teflon-coated stopper. Inject approximately 5 mCi of 99mTc-pertechnetate eluate into the vial and place it in a boiling water bath for 1 hour. HPLC analysis shows a yield of greater than 80% of the [99mTcCl2 (DMPE)2 ]+ complex. Dispense 5 ml into a 10 cc vial and crimp seal it

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: PE lipids (1,2-dilauroyl-sn-glycero-3-phosphoethanolamine, DMPE; 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine, DMPE; 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine, DPPE; 1,2-dioctadecanoyl-sn-glycero-3-phosphoethanolamine, DSPE, Avanti polar lipids. Inc.) were dissolved in 500 uL CHCl3 and 500 uL DMF, 1.2 eq of fluorescein-PEG2000-NHS (creative PEG works Inc.) was added and the reaction mixture were agitated overnight, the amphiphilic fluorescein PEG amphiphiles were purified by reverse phase HPLC using a C4 column (BioBasic-4, 200 mm×4.6 mm, Thermo Scientific), 100 mM triethylamine-acetic acid buffer (TEAA, pH 7.5)-methanol (0-30 min, 10-100%) as an eluent. the amphiphilic fluorescein PEG amphiphiles were purified by reverse phase HPLC a C4 column (BioBasic-4, 200 mm×4.6 mm, Thermo Scientific), 100 mM triethylamine-acetic acid buffer (TEAA, pH 7.5)-methanol (0-30 min, 10-100%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (C6H5)2PCH2CH2P(C6H5)2 ; (CH3CH2)2PCH2CH2P(CH2CH3)2 ; (CH3)2PCH2CH2P(CH3)2; (C6H5)2PCH2P(C6H5)2 ; and [(C6H5)2PCH2CH2 ]2P(C6H5).

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The general process was applied to methyl 3-chlorobenzoate (171 mg, 1.0 mmol). The borylation step was carried out neat with HBPin (200 mg, 1.55 mmol) and dmpe (3.0 mg, 0.02 mmol, 2 mol %) at 150° C. for 3 hours. The oxidation step was then performed as described above, after which the crude material was dissolved in ether and passed through a plug of silica gel (pentane/ether 2:1). Evaporation of solvent gave 134 mg phenol 5 (72%) with trace water. Sublimation at 85° C. under 0.06 mm Hg afforded analytically pure 5 as a white solid; mp 133-135° C. (lit. 138-139). 1H NMR (300 MHz, acetone-d6): δ 9.2 (brs, 1 H), 7.43 (t, J=1.7 Hz, 1 H), 7.40 (dd, J=2.2, 1.7 Hz, 1 H), 7.10 (t, J=2.2 Hz, 1 H), 3.87 (s, 3 H); 13C NMR (75 MHz, acetone-d6): δ 165.9, 159.3, 135.3, 133.8, 121.0, 120.6, 115.7, 52.7; IR (neat): 3335, 1690, 1591, 1431, 1350, 1242, 768 cm−1; LRMS: m/e 186 (M+), 155, 127, 99. Anal. Calcd for C8H7ClO3: C, 51.50; H, 3.78. Found C, 51.78; H, 3.73. For a previous preparation see Takahashi et al., Heterocycles 23: 1483-1491 (1985) (three steps from 3,5-dichlorobenzoic acid, 65% overall yield). Evaporation of solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The general process was applied to methyl 3-chlorobenzoate (171 mg, 1.0 mmol). The borylation step was carried out neat with HBPin (200 mg, 1.55 mmol) and dmpe (3.0 mg, 0.02 mmol, 2 mol %) at 150° C. for 3 hours. The oxidation step was then performed as described above, after which the crude material was dissolved in ether and passed through a plug of silica gel (pentane/ether 2:1). Evaporation of solvent gave 134 mg phenol 5 (72%) with trace water. Sublimation at 85° C. under 0.06 mm Hg afforded analytically pure 5 as a white solid; mp 133-135° C. (lit. 138-139). 1H NMR (300 MHz, acetone-d6): δ 9.2 (brs, 1 H), 7.43 (t, J=1.7 Hz, 1 H), 7.40 (dd, J=2.2, 1.7 Hz, 1 H), 7.10 (t, J=2.2 Hz, 1 H), 3.87 (s, 3 H); 13C NMR (75 MHz, acetone-d6): δ 165.9, 159.3, 135.3, 133.8, 121.0, 120.6, 115.7, 52.7; IR (neat): 3335, 1690, 1591, 1431, 1350, 1242, 768 cm−1; LRMS: m/e 186 (M+), 155, 127, 99. Anal. Calcd for C8H7ClO3: C, 51.50; H, 3.78. Found C, 51.78; H, 3.73. For a previous preparation see Takahashi et al., Heterocycles 23: 1483-1491 (1985) (three steps from 3,5-dichlorobenzoic acid, 65% overall yield). Evaporation of solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The general process was applied to methyl 3-chlorobenzoate (171 mg, 1.0 mmol). The borylation step was carried out neat with HBPin (200 mg, 1.55 mmol) and dmpe (3.0 mg, 0.02 mmol, 2 mol %) at 150° C. for 3 hours. The oxidation step was then performed as described above, after which the crude material was dissolved in ether and passed through a plug of silica gel (pentane/ether 2:1). Evaporation of solvent gave 134 mg phenol 5 (72%) with trace water. Sublimation at 85° C. under 0.06 mm Hg afforded analytically pure 5 as a white solid; mp 133-135° C. (lit. 138-139). 1H NMR (300 MHz, acetone-d6): δ 9.2 (brs, 1 H), 7.43 (t, J=1.7 Hz, 1 H), 7.40 (dd, J=2.2, 1.7 Hz, 1 H), 7.10 (t, J=2.2 Hz, 1 H), 3.87 (s, 3 H); 13C NMR (75 MHz, acetone-d6): δ 165.9, 159.3, 135.3, 133.8, 121.0, 120.6, 115.7, 52.7; IR (neat): 3335, 1690, 1591, 1431, 1350, 1242, 768 cm−1; LRMS: m/e 186 (M+), 155, 127, 99. Anal. Calcd for C8H7ClO3: C, 51.50; H, 3.78. Found C, 51.78; H, 3.73. For a previous preparation see Takahashi et al., Heterocycles 23: 1483-1491 (1985) (three steps from 3,5-dichlorobenzoic acid, 65% overall yield). Evaporation of solvent

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an atmosphere of dry nitrogen, 103 mg 1,5-cyclooctadiene(H5-indenyl)iridium (I) was put in a 25 mL Pyrex bottle. Subsequently were added 0.04 mL 1,2-bis(dimethylphosphino)ethane, 0.61 mL 3-bromochlorobenzene and 1.52 mL pinacolborane. The mixture was stirred at 150° C. for 3.5 h. After cooling to room temperature, the borane adduct was taken up in 17 mL acetone to give a clear solution. This solution was added slowly to 17.41 mL of a 0.30 M solution of oxone in water cooled in an ice bath. The mixture was stirred vigorously for 15 min. at room temperature and extracted three times with DCM. The combined organic phases were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM) to yield 750 mg (62%) of a beige solid. 1H NMR complies with known data (compound (1), Maleczka, 2003). After cooling to room temperature to give a clear solution cooled in an ice bath The mixture was stirred vigorously for 15 min. at room temperature extracted three times with DCM The combined organic phases were dried over Na2SO4 evaporated to dryness The residue was purified by flash chromatography (DCM)