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Norbornadiene

About: Norbornadiene is a research topic. Over the lifetime, 2389 publications have been published within this topic receiving 38603 citations.


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Journal ArticleDOI
TL;DR: Optically active 1-methylpropargyl esters bearing azobenzene groups, namely, (S)-(−)-3-methyl-3-{4]-4-(n-butyloxy)phenylazophenyl]carbonyl}oxy-1-propyne (1), (S −)-3 -methyl -3 -{4 -hexyloxy)-phenyl azophenyl]- carbonyl]oxy- 1-pro pyrene (2) were synthesized and polymerized with Rh+(nbd)[η6-C
Abstract: Optically active 1-methylpropargyl esters bearing azobenzene groups, namely, (S)-(−)-3-methyl-3-{4-[4-(n-butyloxy)phenylazophenyl]carbonyl}oxy-1-propyne (1), (S)-(−)-3-methyl-3-{4-[4-(n-hexyloxy)phenylazophenyl]carbonyl}oxy-1-propyne (2), and (S)-(−)-3-methyl-3-{4-[4-(n-octyloxy)phenylazophenyl]carbonyl}oxy-1-propyne (3) were synthesized and polymerized with Rh+(nbd)[η6-C6H5B−(C6H5)3] (nbd, norbornadiene) as a catalyst to afford the corresponding poly(1-methyloropargyl ester)s with moderate molecular weights (Mn = 24,000–31,300) in good yields (79–84%). Polymers were soluble in common organic solvents including toluene, CHCl3, CH2Cl2, THF, and DMSO, whereas insoluble in diethyl ether, n-hexane, and methanol. Large optical rotations and strong CD signals demonstrated that all the polymers take a helical structure with a predominantly one-handed screw sense. The helical structure of the polymers changed with the addition of MeOH and heat. The trans-azobenzene of the polymer side chains isomerized into cis on UV irradiation, which was accompanied with drastic helical conformational changes of the polymer backbone. The cis-azobenzene moiety reisomerized into trans on visible-light irradiation, which induced the recovery of chiral geometry of azobenzene moieties in the side chain. Conformational analysis revealed that the polymers form a tightly twisted right-handed helical structure with a dihedral angle of 70° at the single bond of the main chain. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 4749–4761, 2009

14 citations

Journal ArticleDOI
TL;DR: In this article, a 1:1 adduct in which Rh and S of the complex are bridged by 5-norbornene-2,3-diyl group is presented.
Abstract: (η-Cyclopentadienyl)(1,2-diphenyl-1,2-ethylenedithiolato)rhodium(III) complex (1) reacts with quadricyclane (Q) to give a 1:1 adduct in which Rh and S of the complex are bridged by 5-norbornene-2,3-diyl group. The adduct dissociates to give 1 and norbornadiene upon irradiation with a medium pressure mercury lamp.

14 citations

Journal ArticleDOI
TL;DR: Isomerically pure exo - and endo -2-mercaptonorbornanes and 2-mercaneenes were prepared by radical addition of the binaphthol-derived thiophosphonates 1a and 1b to norbornene and norbornadiene, separation of the exo and endosomer by flash-chromatography and reduction with lithium aluminium hydride as mentioned in this paper.
Abstract: Isomerically pure exo - and endo -2-mercaptonorbornanes and 2-mercaptonorbornenes were prepared by radical addition of the binaphthol-derived thiophosphonates 1a and 1b to norbornene and norbornadiene, separation of the exo and endo isomers by flash-chromatography and reduction with lithium aluminium hydride. The reaction of 1b with norbornadiene performed with enantiopure 1,1′-binaphthol, produced a 1:1 mixture of the exo -diastereoisomers, one of which could be obtained in pure form by fractional crystallization. The latter, upon reduction with lithium aluminium hydride, afforded enantiomerically pure exo -2-mercaptonorbornene showing that the binaphthylthiophosphonates can be considered as safe, chiral synthetic equivalents of hydrogen sulfide.

14 citations

Journal ArticleDOI
TL;DR: In this article, the crystal structure of [(COD)(Cl)RH(μ-pyrazine)Rh(Cl)(COD)] has been determined and their reactions with carbon monoxide, 2,2′-bipyridine and 1,10phenanthroline investigated.

14 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202316
202240
202133
202040
201930
201829