Bicyclic bases. Synthesis, configuration, and NMR analysis of N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane-2-oxides

Philip S Portoghese, V. G. Telang

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The novel bicyclic system, N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane (IV), was synthesized from tritosylhydroxy-L-prolinol and thioacetate anion. Sodium metaperiodate oxidation of (IV) yielded exclusively the exo sulfoxide (VI) from which the isomeric endo product (VIII) was obtained by treatment with ethyloxonium fluoroborate. Thermally induced equilibration studies demonstrated that the exo-oxide is thermodynamically more stable than the endo-oude. The sulfone (V) was prepared by oxidation with H2O2. The identity of all proton resonances in the 100-MHz NMR spectra of (IV-VI, VIII) were deduced from spin-decoupling experiments.

Original languageEnglish (US)
Pages (from-to)1823-1829
Number of pages7
JournalTetrahedron
Volume27
Issue number10
DOIs
StatePublished - Jan 1 1971

Fingerprint

sulfoxide
Heptanes
Sulfones
Oxides
Anions
Protons
Nuclear magnetic resonance
Oxidation
Experiments
metaperiodate
prolinol

Cite this

Bicyclic bases. Synthesis, configuration, and NMR analysis of N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane-2-oxides. / Portoghese, Philip S; Telang, V. G.

In: Tetrahedron, Vol. 27, No. 10, 01.01.1971, p. 1823-1829.

Research output: Contribution to journalArticle

@article{259fbb0e1fc94f63aa1c1be49b62db68,
title = "Bicyclic bases. Synthesis, configuration, and NMR analysis of N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane-2-oxides",
abstract = "The novel bicyclic system, N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane (IV), was synthesized from tritosylhydroxy-L-prolinol and thioacetate anion. Sodium metaperiodate oxidation of (IV) yielded exclusively the exo sulfoxide (VI) from which the isomeric endo product (VIII) was obtained by treatment with ethyloxonium fluoroborate. Thermally induced equilibration studies demonstrated that the exo-oxide is thermodynamically more stable than the endo-oude. The sulfone (V) was prepared by oxidation with H2O2. The identity of all proton resonances in the 100-MHz NMR spectra of (IV-VI, VIII) were deduced from spin-decoupling experiments.",
author = "Portoghese, {Philip S} and Telang, {V. G.}",
year = "1971",
month = "1",
day = "1",
doi = "10.1016/S0040-4020(01)98215-8",
language = "English (US)",
volume = "27",
pages = "1823--1829",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "10",

}

TY - JOUR

T1 - Bicyclic bases. Synthesis, configuration, and NMR analysis of N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane-2-oxides

AU - Portoghese, Philip S

AU - Telang, V. G.

PY - 1971/1/1

Y1 - 1971/1/1

N2 - The novel bicyclic system, N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane (IV), was synthesized from tritosylhydroxy-L-prolinol and thioacetate anion. Sodium metaperiodate oxidation of (IV) yielded exclusively the exo sulfoxide (VI) from which the isomeric endo product (VIII) was obtained by treatment with ethyloxonium fluoroborate. Thermally induced equilibration studies demonstrated that the exo-oxide is thermodynamically more stable than the endo-oude. The sulfone (V) was prepared by oxidation with H2O2. The identity of all proton resonances in the 100-MHz NMR spectra of (IV-VI, VIII) were deduced from spin-decoupling experiments.

AB - The novel bicyclic system, N-tosyl-2-thia-5-azabicyclo[2.2.1]heptane (IV), was synthesized from tritosylhydroxy-L-prolinol and thioacetate anion. Sodium metaperiodate oxidation of (IV) yielded exclusively the exo sulfoxide (VI) from which the isomeric endo product (VIII) was obtained by treatment with ethyloxonium fluoroborate. Thermally induced equilibration studies demonstrated that the exo-oxide is thermodynamically more stable than the endo-oude. The sulfone (V) was prepared by oxidation with H2O2. The identity of all proton resonances in the 100-MHz NMR spectra of (IV-VI, VIII) were deduced from spin-decoupling experiments.

UR - http://www.scopus.com/inward/record.url?scp=0346848401&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0346848401&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)98215-8

DO - 10.1016/S0040-4020(01)98215-8

M3 - Article

AN - SCOPUS:0346848401

VL - 27

SP - 1823

EP - 1829

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 10

ER -