Structures of photochromic spiroindolinobenzoxazines and a spiroindolinobenzopyran

Osano, Yasuko T.; Mitsuhashi, Kazuo; Maeda, Shuichi; Matsuzaki, Tatsuya

doi:10.1107/s0108270191003499

Cited by 10 publications

(10 citation statements)

References 2 publications

(2 reference statements)

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“…The chromene plane can bend either towards the geminal methyl groups or away from these. Focusing on chromene heterocyles of structural related entries in the CSD (CUTQUQ01 [4], CUTCUQ 02 [10], FURBUP [11], KACLOQ [12], KOCWOO [13]) the same flexibility of the angle is observed (Figure 6b). However, in all structures the typical weakening of the CSpiro-O bond to 1.47 Å is observed, which correspond to the bond length indicated for spiropyrans and spirooxazines in all known crystal structures of the CSD.…”

Section: Discussionmentioning

confidence: 82%

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

et al. 2017

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Abstract:In this work, crystal structures of commercially available photochromic compounds, i.e., spiropyrans and spirooxazines, were investigated by single-crystal X-ray diffraction. A total of five new structures were obtained via isothermal evaporation experiments under different conditions, namely 1,3,3-Trimethylindolino-benzopyrylospiran (I), 1,3,3-Trimethylindolinonaphtospirooxaxine (II), 1-(2-Hydroxyethyl)-3,3-dimethylindolino-6 -nitrobenzopyrylospiran (III), and 1,3,3-Trimethylindolino-8 -methoxybenzopyrylospiran (IVa and IVb). Since the basic structure of a spiropyran/-oxazine does not present typical hydrogen bond accepting and donating groups, this study illustrates the importance of additional functional groups connected to this kind of molecules to induce specific intermolecular interactions. Our results show that possible hydrogen bonding interactions are rather weak due to the high steric demand of these compounds. These results are supported by a search of the Cambridge structural database focused on related structures.

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Section: Discussionmentioning

confidence: 82%

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

et al. 2017

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“…The three spiropyran derivatives 1 – 3 were synthesized according to reported procedures . All of them were obtained as yellowish solids.…”

Section: Resultsmentioning

confidence: 99%

“…Preparation and characterization of spiropyrans 1–3 : Three spiro compounds were synthesized according to reported procedures …”

Section: Methodsmentioning

confidence: 99%

Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization

Ishikawa

Uemura

Saito

et al. 2019

Chemistry A European J

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Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single‐crystal X‐ray analysis and each enantiomorphic crystal was correlated with its solid‐state circular dichroism (CD) spectrum.

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“…The three spiropyran derivatives 1-3 weres ynthesized according to reported procedures. [11][12][13] All of them were obtained as yellowish solids. Figure 3s hows ap ictureo fthec ompounds in both hexane and methanol.…”

Section: Resultsmentioning

confidence: 99%

“…Preparation and characterization of spiropyrans 1-3:T hree spiro compounds were synthesized according to reported procedures. [11][12][13] Chem. Eur.J.…”

Section: Methodsmentioning

confidence: 99%

Making Use of the Direct Process Residue: Synthesis of Bifunctional Monosilanes

Sturm

Santowski

Schweizer

et al. 2019

Chemistry A European J

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The industrial production of monosilanes MenSiCl4−n (n=1–3) through the Müller–Rochow Direct Process generates disilanes MenSi2Cl6−n (n=2–6) as unwanted byproducts (“Direct Process Residue”, DPR) by the thousands of tons annually, large quantities of which are usually disposed of by incineration. Herein we report a surprisingly facile and highly effective protocol for conversion of the DPR: hydrogenation with complex metal hydrides followed by Si−Si bond cleavage with HCl/ether solutions gives (mostly bifunctional) monosilanes in excellent yields. Competing side reactions are efficiently suppressed by the appropriate choice of reaction conditions.

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Structures of photochromic spiroindolinobenzoxazines and a spiroindolinobenzopyran

Cited by 10 publications

References 2 publications

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization

Making Use of the Direct Process Residue: Synthesis of Bifunctional Monosilanes

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