Sulfonpyrolyse als Synthesemethode

Vögtle, Fritz; Rossa, L.

doi:10.1002/ange.19790910705

Cited by 68 publications

(18 citation statements)

References 108 publications

(9 reference statements)

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“…Not only has this route been applied to the preparation of [3.3]-and [4.4]paracyclophane already, [12,[18][19][20][21] but its preparative variability (preparation of functionalized derivatives) and often good yield make it particularly attractive. [22] We hence decided to prepare [3.2]-(10), [4.2]- (14) and [4.3]paracyclophane (19) by this route.…”

Section: Synthesis Of [32]-(10) [42]-(14) and [43]paracyclophane mentioning

confidence: 99%

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Paracyclophanes: Extending the Bridges. Synthesis

2009

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Section: Synthesis Of [32]-(10) [42]-(14) and [43]paracyclophane mentioning

confidence: 99%

“…UV (acetonitrile): λ max (log ε) = 220 (4.05), 213 (4.00), 197 nm (4.45). MS (EI, 70 eV): m/z (%) = 308 (22) …”

Section: -[(Methoxycarbonyl)methyl]-1-[2ј-(methoxycarbonyl)ethyl]benmentioning

confidence: 99%

Paracyclophanes: Extending the Bridges. Synthesis

2009

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“…[34,35] On the other hand, the formation of a [4ϩ4] cycloadduct from o-xylylene generated at higher temperatures by cheletropic extrusion of SO 2 from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide is a known process. [36] In one of our previous papers [26] we described the intramolecular We applied the tricyclic compound 47 and its homologue 48 to the synthesis of the 10,14-diazasteroid framework. Numerous methods directed towards the synthesis of steroid analogues bearing nitrogen atoms in various skeleton positions have been developed.…”

Section: Resultsmentioning

confidence: 99%

Reactions of Pyridine Analogues of Aza-o-xylylenes Generated from 1,3-Dihydroisothiazolo[4,3-b]pyridine 2,2-Dioxides (Pyridosultams) − Formation of 2:1 Adducts withN-Phenylmaleimide

Wojciechowski

Kosinski

2002

Eur. J. Org. Chem.

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“…A very brief structural proof (MS and NMR) for the [2.2.2]m,m,mcyclophane (tri-m-xylylene) as a side product of a Wurtz reaction was given by Jenny and Burri in 1966 [30]. In this paper we report the HD-2SO 2 [4,5,8,23].…”

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Concave π-prismand hydrocarbon [2.2.2]cyclophanes and their crystalline Ag-triflate complexes

et al. 1999

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237High dilution principle and its use as a synthetic tool has been widely recognised and was reviewed by Vögtle in 1991 [1]. Particularly cyclophane [2] and supramolecular chemistry [3] have gained a lot owing to the use of HD principle, in spite of the rather poor yields associated with its use. Another very useful synthetic tool, namely sulfone pyrolysis developed in late 1960's, has been of tremendous help in preparing highly strained (macro)cyclic compounds. Sulfone pyrolysis and its use as a synthesis method has been twice reviewed by Vögtle, first in 1979 [4] and then in 1991 [5]. The combination of these two methods into HD-SO 2 -method (High-dilution cyclisation reaction of a bis-bromide and a bis-thiol to a cyclic n membered bis-sulphide followed by oxidation to the corresponding cyclic bis-sulfone and subsequent extrusion of 2 moles of SO 2 under vacuum and elevated temperatures leading to a (n-2) membered cyclophane), has had a major impact on the synthesis of strained cyclophanes as shown by the pioneering work of Vögtle over more than three decades [6]. Professor Vögtle's impact on the HD-SO 2 -method has also materialised as inventions of specific equipment designed particularly for this type of synthetic work, these include high dilution apparatus [7] (Fig 1.) and ring oven apparatus for the vacuum pyrolysis of sulfones [8] (Fig. 2.).During our ten year collaboration with Professor Vögtle the use of the HD-and HD-SO 2 -method has successfully been employed to the synthesis of helically chiral cyclophanes, bicyclic compounds, extremely strained hydrocarbons, thiaand pyridinophanes and most recently concave hydrocarbon cyclophanes [9 -26].In p,p,p-cyclophane and claimed that it was the first member of a new class of compounds. Owing to its structure and complexation properties they proposed the name π-prismand for such hydrocarbon cyclophanes [28]. Further studies revealed that in the π-prismand-Ag + complex the silver ion is bonded not to the centre of the benzene ring but to edge of the cavity owing to a specific interaction with one carbon-carbon double bond in each phenyl moiety [29] ,m,m-, m,m,p-and m,p,p-cyclophane, the latter two being previously unknown. The complexation with silver triflate was studied for the m,m,p-and m,p,p-cyclophanes.

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Sulfonpyrolyse als Synthesemethode

Cited by 68 publications

References 108 publications

Paracyclophanes: Extending the Bridges. Synthesis

Paracyclophanes: Extending the Bridges. Synthesis

Reactions of Pyridine Analogues of Aza-o-xylylenes Generated from 1,3-Dihydroisothiazolo[4,3-b]pyridine 2,2-Dioxides (Pyridosultams) − Formation of 2:1 Adducts withN-Phenylmaleimide

Concave π-prismand hydrocarbon [2.2.2]cyclophanes and their crystalline Ag-triflate complexes

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