Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane

Yuan Qiang Li; Thies Thiemann; Keisuke Mimura; Tsuyoshi Sawada; Shuntaro Mataka; Masashi Tashiro

doi:10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p

Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane

Yuan Qiang Li
, Thies Thiemann
, Keisuke Mimura
, Tsuyoshi Sawada
, Shuntaro Mataka
, Masashi Tashiro

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

14 Citations (Scopus)

Abstract

The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.

Original language	English
Pages (from-to)	1841-1850
Number of pages	10
Journal	European Journal of Organic Chemistry
Issue number	9
DOIs	https://doi.org/10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p
Publication status	Published - Sept 1998
Externally published	Yes

Keywords

Oxidative Diels-Alder reaction
Thiophenophane S-monoxide
Thiophenophanes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p

Cite this

Li, Y. Q., Thiemann, T., Mimura, K., Sawada, T., Mataka, S., & Tashiro, M. (1998). Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane. European Journal of Organic Chemistry, (9), 1841-1850. https://doi.org/10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p

Li, YQ, Thiemann, T, Mimura, K, Sawada, T, Mataka, S & Tashiro, M 1998, 'Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane', European Journal of Organic Chemistry, no. 9, pp. 1841-1850. https://doi.org/10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p

@article{929b000975b942efb32adcc291b14062,

title = "Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane",

abstract = "The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.",

keywords = "Oxidative Diels-Alder reaction, Thiophenophane S-monoxide, Thiophenophanes",

author = "Li, \{Yuan Qiang\} and Thies Thiemann and Keisuke Mimura and Tsuyoshi Sawada and Shuntaro Mataka and Masashi Tashiro",

year = "1998",

month = sep,

doi = "10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p",

language = "English",

pages = "1841--1850",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

number = "9",

}

TY - JOUR

T1 - Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane

AU - Li, Yuan Qiang

AU - Thiemann, Thies

AU - Mimura, Keisuke

AU - Sawada, Tsuyoshi

AU - Mataka, Shuntaro

AU - Tashiro, Masashi

PY - 1998/9

Y1 - 1998/9

N2 - The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.

AB - The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.

KW - Oxidative Diels-Alder reaction

KW - Thiophenophane S-monoxide

KW - Thiophenophanes

UR - https://www.scopus.com/pages/publications/0002167428

UR - https://www.scopus.com/pages/publications/0002167428#tab=citedBy

U2 - 10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p

DO - 10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p

M3 - Article

AN - SCOPUS:0002167428

SN - 1434-193X

SP - 1841

EP - 1850

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

ER -

Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this