1,2-Diaza-2,4,6,8-cyclooctatetraene

Barry M. Trost, Paul H. Scudder, Robert M. Cory, Nicholas J. Turro, Vaidhyanathan Ramamurthy, Thomas J. Katz

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

1,2-Diazocine is prepared from 7,8-diazatetracyclo[3.3.0.02.4.03,6]oct-7-ene by four methods that excite the precursor into its triplet state of lowest energy. The 1H NMR spectrum shows its structure to be 2 and not 2a and its conformation to be 12. When heated it gives benzene and pyridine, and when irradiated with ultraviolet light it gives only benzene. Reasons are discussed why pyridine is formed in the one reaction and not in the other. The kinetics are recorded for the thermal reaction. Evidence that its double-bond and valence isomers are destabilized because lone pairs of electrons on adjacent nitrogens repel each other is sought in 2's reduction potential, but it cannot be recognized. Valence tautomers 7-11 are not detected in 2 by NMR spectroscopy.

Original languageEnglish
Pages (from-to)1264-1269
Number of pages6
JournalJournal of Organic Chemistry
Volume44
Issue number8
StatePublished - Dec 1 1979
Externally publishedYes

Fingerprint

Benzene
Isomers
Nuclear magnetic resonance spectroscopy
Conformations
Nitrogen
Nuclear magnetic resonance
Kinetics
Electrons
pyridine
Ultraviolet Rays
Hot Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Trost, B. M., Scudder, P. H., Cory, R. M., Turro, N. J., Ramamurthy, V., & Katz, T. J. (1979). 1,2-Diaza-2,4,6,8-cyclooctatetraene. Journal of Organic Chemistry, 44(8), 1264-1269.

1,2-Diaza-2,4,6,8-cyclooctatetraene. / Trost, Barry M.; Scudder, Paul H.; Cory, Robert M.; Turro, Nicholas J.; Ramamurthy, Vaidhyanathan; Katz, Thomas J.

In: Journal of Organic Chemistry, Vol. 44, No. 8, 01.12.1979, p. 1264-1269.

Research output: Contribution to journalArticle

Trost, BM, Scudder, PH, Cory, RM, Turro, NJ, Ramamurthy, V & Katz, TJ 1979, '1,2-Diaza-2,4,6,8-cyclooctatetraene', Journal of Organic Chemistry, vol. 44, no. 8, pp. 1264-1269.
Trost BM, Scudder PH, Cory RM, Turro NJ, Ramamurthy V, Katz TJ. 1,2-Diaza-2,4,6,8-cyclooctatetraene. Journal of Organic Chemistry. 1979 Dec 1;44(8):1264-1269.
Trost, Barry M. ; Scudder, Paul H. ; Cory, Robert M. ; Turro, Nicholas J. ; Ramamurthy, Vaidhyanathan ; Katz, Thomas J. / 1,2-Diaza-2,4,6,8-cyclooctatetraene. In: Journal of Organic Chemistry. 1979 ; Vol. 44, No. 8. pp. 1264-1269.
@article{e3cab69e434440d9b07489bb6e8f704a,
title = "1,2-Diaza-2,4,6,8-cyclooctatetraene",
abstract = "1,2-Diazocine is prepared from 7,8-diazatetracyclo[3.3.0.02.4.03,6]oct-7-ene by four methods that excite the precursor into its triplet state of lowest energy. The 1H NMR spectrum shows its structure to be 2 and not 2a and its conformation to be 12. When heated it gives benzene and pyridine, and when irradiated with ultraviolet light it gives only benzene. Reasons are discussed why pyridine is formed in the one reaction and not in the other. The kinetics are recorded for the thermal reaction. Evidence that its double-bond and valence isomers are destabilized because lone pairs of electrons on adjacent nitrogens repel each other is sought in 2's reduction potential, but it cannot be recognized. Valence tautomers 7-11 are not detected in 2 by NMR spectroscopy.",
author = "Trost, {Barry M.} and Scudder, {Paul H.} and Cory, {Robert M.} and Turro, {Nicholas J.} and Vaidhyanathan Ramamurthy and Katz, {Thomas J.}",
year = "1979",
month = "12",
day = "1",
language = "English",
volume = "44",
pages = "1264--1269",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - 1,2-Diaza-2,4,6,8-cyclooctatetraene

AU - Trost, Barry M.

AU - Scudder, Paul H.

AU - Cory, Robert M.

AU - Turro, Nicholas J.

AU - Ramamurthy, Vaidhyanathan

AU - Katz, Thomas J.

PY - 1979/12/1

Y1 - 1979/12/1

N2 - 1,2-Diazocine is prepared from 7,8-diazatetracyclo[3.3.0.02.4.03,6]oct-7-ene by four methods that excite the precursor into its triplet state of lowest energy. The 1H NMR spectrum shows its structure to be 2 and not 2a and its conformation to be 12. When heated it gives benzene and pyridine, and when irradiated with ultraviolet light it gives only benzene. Reasons are discussed why pyridine is formed in the one reaction and not in the other. The kinetics are recorded for the thermal reaction. Evidence that its double-bond and valence isomers are destabilized because lone pairs of electrons on adjacent nitrogens repel each other is sought in 2's reduction potential, but it cannot be recognized. Valence tautomers 7-11 are not detected in 2 by NMR spectroscopy.

AB - 1,2-Diazocine is prepared from 7,8-diazatetracyclo[3.3.0.02.4.03,6]oct-7-ene by four methods that excite the precursor into its triplet state of lowest energy. The 1H NMR spectrum shows its structure to be 2 and not 2a and its conformation to be 12. When heated it gives benzene and pyridine, and when irradiated with ultraviolet light it gives only benzene. Reasons are discussed why pyridine is formed in the one reaction and not in the other. The kinetics are recorded for the thermal reaction. Evidence that its double-bond and valence isomers are destabilized because lone pairs of electrons on adjacent nitrogens repel each other is sought in 2's reduction potential, but it cannot be recognized. Valence tautomers 7-11 are not detected in 2 by NMR spectroscopy.

UR - http://www.scopus.com/inward/record.url?scp=0004182612&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0004182612&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0004182612

VL - 44

SP - 1264

EP - 1269

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 8

ER -