Proton Magnetic Resonance Spectroscopy: Part I

Coxon, Bruce

doi:10.1016/s0065-2318(08)60397-2

Cited by 35 publications

(2 citation statements)

References 173 publications

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“…Some of the earlier treatments of unsaturated carbohydrates are cited in a review on NMR applications in this field. 586 The half-chair conformation for 3,6-dihydropyran (118) as well as for 1,4-dioxene (122) received further support from a Raman study587 that yielded barriers for ring inversion in the gas phase of 7.6 ± 0.6 kcal/mol for 118 and 122 as well as for cyclohexene.…”

Section: Benzocycloalkenesmentioning

confidence: 94%

Proton nuclear magnetic resonance spectra of cyclic monoenes: hydrocarbons, ketones, heterocycles, and benzo derivatives

Guenther¹,

Jikeli²

1977

Chem. Rev.

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Section: Benzocycloalkenesmentioning

confidence: 94%

Proton nuclear magnetic resonance spectra of cyclic monoenes: hydrocarbons, ketones, heterocycles, and benzo derivatives

Guenther¹,

Jikeli²

1977

Chem. Rev.

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“…With the development of NMR technology, studies became more sophisticated. Horton and co-workers , were at the forefront in studying the conformation of pyranose sugar rings at low temperature and furthermore had the advantage of being among the first in the community with access to a 220 MHz NMR with a superconducting solenoid. This advantage let to a series of papers on the “application of 220 MHz NMR to the solution of stereochemical problems”, where some of them used low-temperature NMR.…”

Section: Historical Aspectsmentioning

confidence: 99%

Mechanisms of Glycosylation Reactions Studied by Low-Temperature Nuclear Magnetic Resonance

2015

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Polyfunktionalisierte Cyclohexane aus Dianhydroinositen. cis ‐1,3(1,4)‐Inosadiamine aus Benzol

et al. 1983

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Die Brauchbarkeit der aus Benzol gut zuganglichen Dianhydroinosite 4 -6 fur die Totalsynthese cis-l,4-bzw. cis-I ,3-disubstituierter Cyclohexantetrole wird exemplarisch belegt. Mit monovalenten Partnern (H20, HI, NaN,, NH2NH2) erfolgt die zweifache Epoxidoffnung jeweils regioselektiv (1,4-Disubstitution) zu den muco-bzw. chiro-Cyclohexan-Derivaten 9, 17 und 26. Mit Hydrazin bzw. N,N'-Dimethylhydrazin als 1,2-Dinucleophilen lassen sich aus 4/5 in guten Ausbeuten (75 -90%) die cis-l,3-Inosadiamine 7g (5-Epistreptamin) und 16g, j (2-Epistreptamin, Actinamin). aus dem weniger symmetrischen 6 in nur bescheidener Ausbeute (ca. 50%) ein Cemisch von 25g (Streptamin) und 27g herstellen. Die von 4 -6 ausgehenden Epoxidoffnungen sind kinetisch so wenig differenziert, da8 eine selektive Einfachoffnung nicht moglich ist.Polyfunctionalised Cyclohexanes from Dianhydroinositols. cis-l,3(1,4)-Inosadiamines from BenzeneThe preparative value of the dianhydroinositols 4 -6, which are readily available from benzene, for the total synthesis of cis-1,4-and cis-1.3-disubstituted cyclohexanetetrols is demonstrated. With monovalent reagents (H,O, HI, NaN,, NH2NH2) the twofold epoxide opening proceeds regioselectively (1,4-disubstitution) yielding the muco-and chiro-cyclohexane derivatives 9, 17, and 26. With hydrazine and N,N'-dimethylhydrazine as 1,2-dinucleophiles the cis-I ,3-inosadiamines 7g (5-epistreptamine) and 16g, j (2-epistreptamine, actinamine) are obtained from 4/5 in good yields . From the less symmetrical 6, however, only the mixture of 25g (streptamine) and 27g is produced in modest yield (ca. 50%). The epoxide opening reactions starting from 4 -6 are kinetically so similar that a selective opening is not possible.Im Zusammenhang mit der Synthese des cis-Trioxa-tris-o-homobenzols 3 (cis-,,Benzoltrioxid", Trisanhydro-cis-inosit) haben wir ein leistungsfahiges Verfahren fur die Herstellung der Epoxycyclohexenylbromide A bzw. B entwickelt (Schema 1)'). Damit waren neben 3 auch die Desoxydianhydroinosite*) (Dianhydroquercite) 1/2 und die Dianhydroinosite 4 -6 derart einfach und okonomisch aus Benzol zuganglich geworden'), daR ein breiter praparativer Einsatz im Bereich polyfunktionalisierter Cyclohexane und speziell fur Aminocyclit-Synthesen attraktiv wurde.

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Proton Magnetic Resonance Spectroscopy: Part I

Cited by 35 publications

References 173 publications

Proton nuclear magnetic resonance spectra of cyclic monoenes: hydrocarbons, ketones, heterocycles, and benzo derivatives

Proton nuclear magnetic resonance spectra of cyclic monoenes: hydrocarbons, ketones, heterocycles, and benzo derivatives

Mechanisms of Glycosylation Reactions Studied by Low-Temperature Nuclear Magnetic Resonance

Polyfunktionalisierte Cyclohexane aus Dianhydroinositen. cis ‐1,3(1,4)‐Inosadiamine aus Benzol

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