Ring opening of 3-methoxyacenaphthylene-1,2-dione. Application of 13C-2D-inadequate-N.M.R. spectroscopy to structure assignment of some substituted naphthalenes.

D. Becker; L. Gottlieb; H. J.E. Loewenthal

doi:10.1016/s0040-4039(00)83877-0

Ring opening of 3-methoxyacenaphthylene-1,2-dione. Application of ¹³C-2D-inadequate-N.M.R. spectroscopy to structure assignment of some substituted naphthalenes.

D. Becker
, L. Gottlieb
, H. J.E. Loewenthal

Technion-Israel Institute of Technology

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Oxidative alkaline cleavage of the title compound 3 gave unexpectedly in high yields the α-keto acid 9a instead of the aldehyde acid 5 (or its tautomer 7). The latter could be prepared via regioselective mono-ketalisation of compound 3. The structure assignment of 9, and differentiation between 5/7 and the isomer 10, were effected using natural abundance ¹³C¹³C coupling techniques.

Original language	English
Pages (from-to)	3775-3776
Number of pages	2
Journal	Tetrahedron Letters
Volume	27
Issue number	32
DOIs	https://doi.org/10.1016/s0040-4039(00)83877-0
State	Published - 1986
Externally published	Yes

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title = "Ring opening of 3-methoxyacenaphthylene-1,2-dione. Application of 13C-2D-inadequate-N.M.R. spectroscopy to structure assignment of some substituted naphthalenes.",

abstract = "Oxidative alkaline cleavage of the title compound 3 gave unexpectedly in high yields the α-keto acid 9a instead of the aldehyde acid 5 (or its tautomer 7). The latter could be prepared via regioselective mono-ketalisation of compound 3. The structure assignment of 9, and differentiation between 5/7 and the isomer 10, were effected using natural abundance 13C13C coupling techniques.",

author = "D. Becker and L. Gottlieb and Loewenthal, \{H. J.E.\}",

year = "1986",

doi = "10.1016/s0040-4039(00)83877-0",

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pages = "3775--3776",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Ring opening of 3-methoxyacenaphthylene-1,2-dione. Application of 13C-2D-inadequate-N.M.R. spectroscopy to structure assignment of some substituted naphthalenes.

AU - Becker, D.

AU - Gottlieb, L.

AU - Loewenthal, H. J.E.

PY - 1986

Y1 - 1986

N2 - Oxidative alkaline cleavage of the title compound 3 gave unexpectedly in high yields the α-keto acid 9a instead of the aldehyde acid 5 (or its tautomer 7). The latter could be prepared via regioselective mono-ketalisation of compound 3. The structure assignment of 9, and differentiation between 5/7 and the isomer 10, were effected using natural abundance 13C13C coupling techniques.

AB - Oxidative alkaline cleavage of the title compound 3 gave unexpectedly in high yields the α-keto acid 9a instead of the aldehyde acid 5 (or its tautomer 7). The latter could be prepared via regioselective mono-ketalisation of compound 3. The structure assignment of 9, and differentiation between 5/7 and the isomer 10, were effected using natural abundance 13C13C coupling techniques.

UR - https://www.scopus.com/pages/publications/0009336364

U2 - 10.1016/s0040-4039(00)83877-0

DO - 10.1016/s0040-4039(00)83877-0

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AN - SCOPUS:0009336364

SN - 0040-4039

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EP - 3776

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Ring opening of 3-methoxyacenaphthylene-1,2-dione. Application of ¹³C-2D-inadequate-N.M.R. spectroscopy to structure assignment of some substituted naphthalenes.

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