Hydroxyalky and Olefinic Substituted gem-Dimethylcyclobutanes

Park, J. D.; Allphin, N. L.; Choi, Sung-Rak; Settine, R. L.; Hedrick, Glen W.

doi:10.1021/i360015a001

Cited by 2 publications

(4 citation statements)

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“…1,5-Diamine 19 was synthesized from previously known dimesylate 18 (Scheme 4), which had been obtained from norpinic acid [31]. The procedure was similar to that described above for the preparation of amines 4 and 10 .…”

Section: Resultsmentioning

confidence: 99%

“…Diamine 19 was prepared from dimesylate 18 [31] as described above for the synthesis of diamine 4 and used in the next step without further purification. tert -Butyl bromoacetate (3.7 mL, 25.1 mmoL) was added dropwise to a mixture of crude diamine 19 (0.45 g, 3.2 mmoL), potassium iodide (2.8 g, 17 mmoL), and DIPEA (8.7 mL, 50.2 mmoL) in anhydrous DMF (15 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Moreover, highly rigid polydentate ligands for metal cations were synthesized as well from norpinic acid [31], which is easily obtained from verbenone (Scheme 1) or pinene. Related ligands, previously described in the literature, have formed gadolinium complexes with interesting properties as potential candidates to contrast agents for magnetic resonance imaging [32,33,34], or complexes with other cations of application in radiopharmacy [35] or for industrial purposes [36].…”

Section: Introductionmentioning

confidence: 99%

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Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands

Illa

Serra

Ardiaca

et al. 2019

IJMS

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Efficient and versatile synthetic methodologies are reported for the preparation of products that are suitable candidates to be used as surfactants, gelators for hydroxylic solvents or metal cation ligands, with potential use in several fields including biomedical applications. The common structural feature of all the synthesized products is the presence of a cis or trans-1,2- or cis-1,3-difunctionalized cyclobutane ring. In the two first cases, the key intermediates including enantiomerically pure 1,3-diamines and 1,3-amino alcohols have been prepared from β-amino acid derivatives obtained, in turn, from a chiral half-ester. This compound is also precursor of γ-amino esters. Furthermore, two kind of polydentate ligands have also been synthesized from a symmetric 1,5-diamine obtained from norpinic acid, which was easily prepared from commercial verbenone.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands

Illa

Serra

Ardiaca

et al. 2019

IJMS

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“…Park et al (2) used LAH reduction of a number of similar materials giving a number of hydroxyalkyl and olefinic substituted gem-dimethylcyclobutanes without complications from isomerization or rearrangement. Park and coworkers also studied the pyrolysis and rearrangement of IIA (3).…”

Section: Discussionmentioning

confidence: 99%

Copper chromite reduction of ethyl pinonate

Lewis¹,

Hedrick²,

Settine³

1969

J. Chem. Eng. Data

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A correlation of molecular flexibility with ring size is also possible in both types of ethers I11 and IV. Compounds V, VI, and VII, which differ only in number of ring difluoromethylene groups (from four-to six-membered rings), vary in order of 0°F. viscosity in ring-size order of 6 >> 4 > 5. The same relationship in the Type IV ethers establishes the better fluid properties of perfluorinated cyclopentane and cyclobutane systems over cyclohexane systems.The thermal stabilities of most of these ethers averaged about 500°F., although V and VI1 ethers had stabilities above 550" F., with the high fluorine content of both ether types resulting in good fire resistance properties. The perfluorocyclobutene trimer, XV, was an extremely mobile fluid with a viscosity of 117 cs. a t -65"F., compared to the acyclic n-CI2Fz6, which is a solid a t 167" F. The thermal stability of XV was above 900" F., as measured by a pressure isoteniscope.

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Hydroxyalky and Olefinic Substituted gem-Dimethylcyclobutanes

Cited by 2 publications

References 5 publications

Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands

Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands

Copper chromite reduction of ethyl pinonate

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