Ein neuer syntheseweg in die paracyclophanreihe photolyse der 2,11-dithia [3.3] paracyclophane

Bruhin, J.; Jenny, W.

doi:10.1016/s0040-4039(01)95800-9

Cited by 48 publications

(22 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Variation of reaction parameters such as concentration (Procedures B, C ) , temperature, or solvent viscosity (Procedure D) did not give improved yields. Attempts to prepare 1 by thermal ([24], Procedure E) or photochemical ( [25], Procedure F) extrusion of sulfur from 1,6-dithiacyclodeca-3,8-diyne (4, X = S) were unsuccessful.…”

Section: )mentioning

confidence: 99%

1,5‐Cyclooctadiyne. Preparation and Reactivity

Kloster‐Jensen

Wirz

1975

Helvetica Chimica Acta

View full text Add to dashboard Cite

Kfingclbergstrasee 80, CH-4056 Basel. Switzcrlmd (20. XI. 74) Summauy. 1,.5-Cyclooctadiyne 1 was isolated in 2 pcrcent yield from polymerized butatrieno 5. Other oligomcrs of 5 wcre dctected in the reaction mixture by combined GLC./MS. analysis but have not been identified. Diets-Aldev adducts of I with two equivalents of 1,J-butadiene and of 2,3-dimethyI-l.J-butarli~ne have bcan preparcd. In the prescnce of strong base 1 isomorizcd to cyclooctatctraenc. 5 was rcformcd by photolysis of 1. Attcmpts to preparc transition mctal complexes of 1 failed. Effrxts of ring strain and of transannular interaction on the rcactivity of 1 arc discusscd. The dirnerization of 5 to 1 is predicted to be strongly cxothcrmic.The synthesis of medium-sized cyclic alkynes [l] and the investigation of their chemical reactivity as a function of geometric ring strain have been the object of considerable effort during the past twenty years. The smallest unsubstituted cycloalkyne yet isolated is cyclooctyne which was first prepared by Bloquist in 1953 [2], Evidence for the intermediate existence of the lower homologues cycloheptyne, .-hexyne, and -pentyne is limited to trapping and self-trapping reactions [3aJ. ' 1 2 3 4 ---1) Permanent addrcss:

show abstract

Section: )mentioning

confidence: 99%

1,5‐Cyclooctadiyne. Preparation and Reactivity

Kloster‐Jensen

Wirz

1975

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…The Ή-ηπίΓ data obtained for the dihydropyrenes gave good support to the hypothesis that equivalent Kekulé structures lead to stronger diatropism (aromaticity). 29 It would appear that the latter method, namely 25 to 22, is the optimum route to 22. Parham 23-2 5 reported the preparation and reactions of a series of alkyl-bridged 1,3-naphthalenes, generally with a substituent in the 2 position, e.g., compound 16.…”

Section: A (13)naphthalene Cyclophanesmentioning

confidence: 99%

Condensed Benzenoid Cyclophanes

Reiss

1983

Organic Chemistry: A Series of Monographs

View full text Add to dashboard Cite

“…An example of a dimeric heterophane that features a nitrogen heterocycle instead of benzene is [2](1,4)benzeno[2](2,5)pyridinophane (pyridinophane 1 ), which was first mentioned in literature in 1972, although the compound was obtained only in poor yields of 1 % . In 1973, an improved synthesis with better yields (60 %) was reported . An alternative synthesis from commercially available precursors was reported by Vögtle et al., but it was only recently, that a simplification of this synthetic route with multigram yields was published .…”

Section: Introductionmentioning

confidence: 99%

Polylutidines: Multifunctional Surfaces through Vapor‐Based Polymerization of Substituted Pyridinophanes

Gall

Hussal

Kramer

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

We report a new class of functionalized polylutidine polymers that are prepared by chemical vapor deposition polymerization of substituted [2](1,4)benzeno[2](2,5)pyridinophanes. To prepare sufficient amounts of monomer for CVD polymerization, a new synthesis route for ethynylpyridinophane has been developed in three steps with an overall yield of 59 %. Subsequent CVD polymerization yielded well-defined films of poly(2,5-lutidinylene-co-p-xylylene) and poly(4-ethynyl-2,5-lutidinylene-co-p-xylylene). All polymers were characterized by infrared reflection-absorption spectroscopy, ellipsometry, contact angle studies, and X-ray photoelectron spectroscopy. Moreover, ζ-potential measurements revealed that polylutidine films have higher isoelectric points than the corresponding poly-xylylene surfaces owing to the nitrogen atoms in the polymer backbone. The availability of reactive alkyne groups on the surface of poly(4-ethynyl-2,5-lutidinylene-co-p-xylylene) coatings was confirmed by spatially controlled surface modification by means of Huisgen 1,3-dipolar cycloaddition. Compared to the more hydrophobic poly-p-xylylyenes, the presence of the heteroatom in the polymer backbone of polylutidine polymers resulted in surfaces that supported an increased adhesion of primary human umbilical vein endothelial cells (HUVECs). Vapor-based polylutidine coatings are a new class of polymers that feature increased hydrophilicity and increased cell adhesion without limiting the flexibility in selecting appropriate functional side groups.

show abstract

Ein neuer syntheseweg in die paracyclophanreihe photolyse der 2,11-dithia [3.3] paracyclophane

Cited by 48 publications

References 5 publications

1,5‐Cyclooctadiyne. Preparation and Reactivity

1,5‐Cyclooctadiyne. Preparation and Reactivity

Condensed Benzenoid Cyclophanes

Polylutidines: Multifunctional Surfaces through Vapor‐Based Polymerization of Substituted Pyridinophanes

Contact Info

Product

Resources

About