Aromatic ring-system controls π-facial selectivity in Diels-Alder reactions of [3.3]orthoanthracenophanes

Shuntaro Mataka; Jiang Ma; Thies Thiemann; Jerzy M. Rudziñski; Tsuyoshi Sawada; Masashi Tashiro

doi:10.1016/0040-4039(95)01230-F

Aromatic ring-system controls π-facial selectivity in Diels-Alder reactions of [3.3]orthoanthracenophanes

Shuntaro Mataka
, Jiang Ma
, Thies Thiemann
, Jerzy M. Rudziñski
, Tsuyoshi Sawada
, Masashi Tashiro

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

15 Citations (Scopus)

Abstract

The Diels-Alder reaction of layered [3.3]orthoanthracenophanes with electrondashpoor dienophiles is studied. Of special interest is the anthracenonaphthophane, which was found to add naphthoquinone, maleic anhydride and maleimide favorably from the inside face and N-phenyltriazolindione and dimethyl azodicarboxylate to the outside.

Original language	English
Pages (from-to)	6105-6108
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	34
DOIs	https://doi.org/10.1016/0040-4039(95)01230-F
Publication status	Published - Aug 21 1995
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)01230-F

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abstract = "The Diels-Alder reaction of layered [3.3]orthoanthracenophanes with electrondashpoor dienophiles is studied. Of special interest is the anthracenonaphthophane, which was found to add naphthoquinone, maleic anhydride and maleimide favorably from the inside face and N-phenyltriazolindione and dimethyl azodicarboxylate to the outside.",

author = "Shuntaro Mataka and Jiang Ma and Thies Thiemann and Rudzi{\~n}ski, \{Jerzy M.\} and Tsuyoshi Sawada and Masashi Tashiro",

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T1 - Aromatic ring-system controls π-facial selectivity in Diels-Alder reactions of [3.3]orthoanthracenophanes

AU - Mataka, Shuntaro

AU - Ma, Jiang

AU - Thiemann, Thies

AU - Rudziñski, Jerzy M.

AU - Sawada, Tsuyoshi

AU - Tashiro, Masashi

PY - 1995/8/21

Y1 - 1995/8/21

N2 - The Diels-Alder reaction of layered [3.3]orthoanthracenophanes with electrondashpoor dienophiles is studied. Of special interest is the anthracenonaphthophane, which was found to add naphthoquinone, maleic anhydride and maleimide favorably from the inside face and N-phenyltriazolindione and dimethyl azodicarboxylate to the outside.

AB - The Diels-Alder reaction of layered [3.3]orthoanthracenophanes with electrondashpoor dienophiles is studied. Of special interest is the anthracenonaphthophane, which was found to add naphthoquinone, maleic anhydride and maleimide favorably from the inside face and N-phenyltriazolindione and dimethyl azodicarboxylate to the outside.

UR - https://www.scopus.com/pages/publications/0029133191

UR - https://www.scopus.com/pages/publications/0029133191#tab=citedBy

U2 - 10.1016/0040-4039(95)01230-F

DO - 10.1016/0040-4039(95)01230-F

M3 - Article

AN - SCOPUS:0029133191

SN - 0040-4039

VL - 36

SP - 6105

EP - 6108

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Aromatic ring-system controls π-facial selectivity in Diels-Alder reactions of [3.3]orthoanthracenophanes

Abstract

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