The Chemistry of Cyclopentadienylmanganese Tricarbonyl Compounds. II. Sulfonation and Metallated Derivatives<sup>1</sup>

Cais, Michael; Kozikowski, John

doi:10.1021/ja01506a029

Cited by 34 publications

(6 citation statements)

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“…Dicyclopentadienyl iron can be mono-or disulfonated with acetyl sulfate in the range 25 to 46°d epending on the amount of reagent used (544); the two sulfonic groups are on different rings. The same reagent sulfonates cyclopentadienyl manganese tricarbonyl in excellent yield (112). Dicyclopentadienyl iron carboxylic acid, and its methyl ester, were monosulfonated on the ring without the carboxyl group with S03-dioxane at 0°( 343).…”

Section: E Miscellaneous Heterocyclic Compoundsmentioning

confidence: 99%

The Reactions of Sulfur Trioxide, and Its Adducts, with Organic Compounds.

Gilbert¹

1962

Chem. Rev.

173

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Section: E Miscellaneous Heterocyclic Compoundsmentioning

confidence: 99%

The Reactions of Sulfur Trioxide, and Its Adducts, with Organic Compounds.

Gilbert¹

1962

Chem. Rev.

173

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“…Many different substituents have been described in literature. [29][30][31][32][33][34][35] However, reports for coupling biologically active targeting vectors are comparably scarce. Being part of the spacer between the chelator and the biovector, the functional group attached to Cp is of great importance for a bifunctional chelator (BFC).…”

Section: Resultsmentioning

confidence: 99%

[(Cp-R)M(CO)3] (M= Re or 99mTc) Conjugates for Theranostic Receptor Targeting

Can

Schmutz

Sulieman

et al. 2013

Chimia

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Cyclopentadienyl complexes of 99mTc became accessible via a retro Diels-Alder synthetic approach of dimerized cyclopentadiene derivatives. So far, this approach was limited to derivatives comprising a carboxylic acid group, directly conjugated to the Cp-ring, leading to complexes [(C5H5COOH)99mTc(CO)3] and [(C5H5CONH-R)99mTc(CO)3], respectively. The introduction of an -NCO group via Curtius rearrangement and subsequent in situ reactions with alcohols or amines gave [(C5H5NHCO-OR)2] and [(C5H5NHCO-NHR)2]. To increase the spacer lengths between the Cp-ring and the functional groups, methylene and ethylene spacers were introduced to yield C5H5-CH2COOH and C5H5-C2H4COOH respectively. The latter Cp-derivatives reacted with [99mTcO4)]- and in the presence of CO releasing/reducing agents to the corresponding [(C5H5-spacer-COOH)99mTc(CO)3] complexes. The carboxylato groups can be derivatized with targeting functions, leading to structurally altered receptor binding complexes, with 99mTc for imaging and with rhenium for therapy. The nature of the 99mTc complexes was assessed by HPLC comparison with the corresponding rhenium compounds.

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“…purified by column chromatography, using a column of 32 X 3 cm packed with 100-200 mesh silica gel, and n-hexane as eluent: ir µ61" 3080, 2945, 1495, 758, 725, 700 cm'1; nmr (100 MHz, CCh) S 1.22 (d, J = 7.0 Hz, 3, CH,), 1.35 (s, 3, CH,), 1.59 and 1.72 (d, 1, CH), 2.04-2.13 (two sets of q, 1, CH), 2.50-2.88 and 3.10-3.33 (both m, 4, benzylic), and 6.64-7.27 ppm (m, 8, aromatic); mass spectrum m/e (rel intensity) 248 (100), 249 (24), 233 (70), 205 (27), 119 (26), 91 (9); mass, caled for CioH20, 248.1565 (found, 248.1567).…”

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confidence: 99%

“…Further Cyclodehydration Reaction of 4-Benzyl-l-tetralol (9).-(1) Water was distilled away from 3.0 ml of 85% phosphoric acid put into a small pear-shaped flask having a thermometer well, until the temperature rose to 240°. To this acid was then added 0.5 g of 4-benzyl-l-tetralol (9), and the temperature was kept at 230-240°for 20 min. Upon cooling, the reaction mixture was poured into a beaker of water.…”

mentioning

confidence: 99%