ChemInform Abstract: SYNTH. UND EIGENSCHAFTEN VON SYMM.‐OKTAHYDROXANTHENEN

Харченко, В. Г.; Yartseva, N. M.; Kozhevnikova, N. I.

doi:10.1002/chin.197315274

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several methods were investigated for preparation of BuOHA ( 9 , Scheme ). Direct alkylation of OHA or corresponding pyrylium salts proved less useful than a two-step approach involving tricyclic keto alcohol 7 . This crystalline intermediate can be easily prepared in 500-g batches by condensation of pentanal with cyclohexanone .…”

Section: Resultsmentioning

confidence: 99%

Molecular Architecture. 2.¹Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

et al. 1998

View full text Add to dashboard Cite

Methods are described for the synthesis of a series of functionalized derivatives of 9-butyl-1,2,3,4,5,6,7,8-octahydroacridine (9), a building block for several types of highly preorganized host compounds. A key intermediate is 5-benzylidene-9-butyl-2,3,5,6,7,8-hexahydroacridin-4(1H)-one ( 23), which can also be used in the syntheses of torands and hydrogen-bonding hexagonal lattice receptors. A tridentate cleft (20), consisting of 2,2′;6′,2′′-terpyridine imbedded in a heptacyclic framework, and a corresponding pentadentate diketone (6) were synthesized from 9 in five and seven steps, respectively. The picrate extraction method was used to estimate the solution stabilities of alkali metal complexes of heptacyclic terpyridyls 6 and 20, which was also compared with a flexible terpyridyl (37). Alkali metal complexes of both heptacyclic terpyridyls showed relatively high K s values, but low size selectivity. Pentadentate host 6 binds Na + and K + more strongly than do most hexadentate crown ethers; flexible tridentate analogue 37 failed to extract alkali metal picrates into chloroform. The complexation abilities of 6 and 20 are attributed to enforced orientation of functional group dipoles toward the center of the molecular cleft. Sodium and potassium picrate complexes of pentadentate cleft 6 were synthesized (1:1 stoichiometry), and a 2:1 complex of calcium triflate (6 2 ‚Ca(CF 3 SO 3 ) 2 ) was also prepared.The discovery of alkali metal complexation by crown ethers 2 foreshadowed development of several other host families, 3 including podands, cryptands, 4 lariat ethers, 5 spherands, 6 cryptahemispherands, 6c and torands. 7 The examples shown in Figure 1 illustrate the general trend toward ion encapsulation and ligand rigidity for cryptands, spherands and cryptaspherands, compared with crown ethers. These structural modifications generally produce higher selectivity and stronger binding of alkali metals

show abstract

Section: Resultsmentioning

confidence: 99%

Molecular Architecture. 2.¹Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

et al. 1998

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: SYNTH. UND EIGENSCHAFTEN VON SYMM.‐OKTAHYDROXANTHENEN

Abstract: Das Oktahydroxanthyliumperchlorat (II) läßt sich in Diäthyläther mit LiAlH4 bzw. den Grignard‐Verbindungen (III) zu den Oktahydroxanthenen (I) und (IV) umsetzen.

Cited by 1 publication

References 0 publications

Molecular Architecture. 2.¹Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

Molecular Architecture. 2.¹Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

Contact Info

Product

Resources

About

ChemInform Abstract: SYNTH. UND EIGENSCHAFTEN VON SYMM.‐OKTAHYDROXANTHENEN

Abstract: Das Oktahydroxanthyliumperchlorat (II) läßt sich in Diäthyläther mit LiAlH4 bzw. den Grignard‐Verbindungen (III) zu den Oktahydroxanthenen (I) und (IV) umsetzen.

Cited by 1 publication

References 0 publications

Molecular Architecture. 2.1Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

Molecular Architecture. 2.1Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

Contact Info

Product

Resources

About

Molecular Architecture. 2.¹Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

Molecular Architecture. 2.¹Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts