The Structures of Substituted o-Quinone Methide Trimers

Merijan, Ashot; Shoulders, Ben A.; Gardner, Pete D.

doi:10.1021/jo01043a507

Cited by 22 publications

(16 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis of 5,12-Dihydro-5, 12-[2' ,3 '-6 [thienonaphthacene (8).•-The synthesis of the triptycene (8) is analogous to that of benzotriptycene (10).7 The starting material, naphtho [2,[3][4][5][6] [thiophene (5), was made essentially according to the work of Carruthers8 in an overall yield of 30%, based on 2-iodothiophene. Addition of copper(II) sulfate9 to the intermediate keto acid 3 during the reduction to acid 4 raised the (1) P. D. Bartlett and S. Cohen, J. Amer. Chem.…”

Section: Resultsmentioning

confidence: 99%

“…Nmr Spectra of Some Thiophene Analogs of Anthracene.-The nmr spectra of benzo [1,2-6:5,4-6']dithiophene (11), of naphtho[2,3-6[thiophene (5), and of 4-acetoxynaphtho [2,3-6[thiophene (19) are given in Table III. There are four kinds of protons in these molecules: meso-anthracenelike protons (1 and 2), naphthalenelike protons (3), and benzene-thio-(13) J. van Reyendam, HMO computer program, University of Groningen, The Netherlands.…”

Section: Resultsmentioning

confidence: 99%

“…yield from 30 to 90% in this step. When 1,4-dihydro-1,4-epoxy naphthalene (6)10 was heated during 48 hr at 195°with naphtho [2,[3][4][5][6] [thiophene (5), the adduct 7 was obtained in 70% yield (Scheme I). The Scheme I 195°4 8hr 5 6 an unsubstituted asymmetric triptycene has not yet been reported.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of an asymmetric heterotriptycene

Wynberg¹,

Wit²,

Sinnige³

1970

J. Org. Chem.

View full text Add to dashboard Cite

This paper describes the synthesis of an unsubstituted heterocyclic asymmetric triptycene, 5,12-dihydro-5,12-[2',3'-6]thienonaphthacene (8). The choice of the starting materials in this synthesis, naphtho [2,3-6]thiophene (5) and 1,4-epoxy-l,4-dihydronaphthalene (6), is based in part on Hückel molecular orbital computations and in part on experimental data.Triptycene (l)1,a has a rigid "propeller" structure and Csh symmetry. Triptycenes are asymmetric when every one of the three aromatic rings is unlike the other two. This asymmetry can be achieved by attaching substituents at appropriate positions, as done by Ogura (2),3,4 or by having every ring inherently different from the other two. An example of

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of an asymmetric heterotriptycene

Wynberg¹,

Wit²,

Sinnige³

1970

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…In Scheme 3 a reaction mechanism for the formation of the macrocycles is proposed. It is believed that after deprotonation of the OH group and subsequent chloride loss of 4 an o -quinoid structure 9 is formed in situ, that quickly reacts with the deprotonated thiol 10 via Michael addition ( Scheme 3 , route A) [ 28 – 30 ]. However, as aromatic thiols at the benzylic position are good leaving groups, conversely β-elimination (route B) can easily occur, leading to reversal of the addition reactions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and post-functionalization of alternate-linked-meta-para-[2ⁿ.1ⁿ]thiacyclophanes

Leger¹,

Adriaensen²,

Robeyns³

et al. 2018

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

In recent decades, considerable research attention has been devoted to new synthetic procedures for thiacyclophanes. Thiacyclophanes are widely used as host molecules for the molecular recognition of organic compounds as well as metals. Herein, we report the selective and high-yielding synthesis of novel alternate-linked-meta-para-thiacyclophanes. These novel thiacyclophanes are selectively synthesized in high-yielding procedures. Furthermore, post-functionalization of the phenolic moieties was successfully performed. The 3D structure of the alternate-linked-meta-para-[22.12]thiacyclophane was further elucidated via X-ray crystallographic analysis.

show abstract

“…65 Reduction of 188 by LiAlH4 generated o-cresol 189; addition between 188 and methylmagnesium iodide generated o-ethylphenol; and warming 188 to room temperature generated trimer 191. 66…”

Section: Scheme 45mentioning

confidence: 99%