1987
DOI: 10.1002/chin.198702148
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ChemInform Abstract: A Hydrocarbon Skeleton with Twelve Identical Functional Groups: Synthesis of a Dodeca Host Compound.

Abstract: 148ChemInform Abstract Synthesis of the symmetrical acetylene (VII) from dimethyliodobenzene(I) is achieved in six steps. Palladium-catalyzed trimerisation of (VII) yields the twelvefold ether (VIIIa). The cleavage of the ether bonds by acetyl bromide and borontrifluoride etherate, and subsequent reaction with the sodium salt of p-toluene thiol produce the dodeca host (VIIIc). (NMR-data).

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Cited by 2 publications
(3 citation statements)
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“…The residue was purified by column chromatography (SiO 2 , petroleum ether) to obtain 2 as white solid (1.8 g, 54%). The spectroscopic data are consistent with the literature …”
Section: Methodssupporting
confidence: 91%
See 1 more Smart Citation
“…The residue was purified by column chromatography (SiO 2 , petroleum ether) to obtain 2 as white solid (1.8 g, 54%). The spectroscopic data are consistent with the literature …”
Section: Methodssupporting
confidence: 91%
“…Scheme illustrates the synthesis of oPE/oPPV aldehyde 7 terminated with two pyridyl groups, and the preparation of the corresponding C 60 -dipyr conjugates ( 8 and 10 ). Specifically, 1,3-bis­(bromomethyl)-5-iodobenzene 2 was prepared from commercially available1-iodo-3,5-dimethylbenzene 1 in 54% yield according to a Wohl–Ziegler reaction following a modified method . Subsequent treatment with an excess of P­(OEt) 3 under Michaelis–Arbuzov conditions afforded bis­(phosphonate) 3 in 88% yield .…”
Section: Resultsmentioning
confidence: 99%
“…The syntheses of intermediates 17 and 36 required for the preparation of unconjugated PBD-dimers and related linker drugs described above are illustrated in Scheme . Commercially available diester 44 was reduced to afford diol 45 , which was subsequently transformed into dibromide 46 in a moderate overall yield on >100 g scale . Coupling of 46 with commercially available 4-hydroxy-3-methoxybenzaldehyde (vanillin) provided intermediate 47 , and this entity was oxidized via the combination of NaClO 2 , NaH 2 PO 4 ·2H 2 O, and H 2 O 2 to give diacid 48 in good yield.…”
Section: Resultsmentioning
confidence: 99%