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Stable derivatives of stannabenzene have been isolated. The 2-stannanaphthalene depicted below is stable in an inert atmosphere at temperatures below 140 °C. The tin to carbon bond in this compound is shielded from potential reactants by two very bulky groups, one
553:
Mizuhata, Yoshiyuki; Sasamori, Takahiro; Takeda, Nobuhiro; Tokitoh, Norihiro (2006). "A Stable
Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene".
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Ebrahimi, Arash Afshar; Ghiasi, Reza; Foroutan-Nejad, Cina (2010). "Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes".
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Yoshiyuki
Mizuhata, Nobuhiro Takeda, Takahiro Sasamori and Norihiro Tokitoh Chemistry Letters Volume 34 Number 8 Year 2005 Page 1088
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402:(201.6 pm). The C-C bonds show little variation with bond lengths between 135.6 and 144.3 pm signaling that this compound is
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Tbt-substituted stannabenzene was reported in 2010. At room-temperature it quantitatively forms the
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Yoshiyuki
Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784
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which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=C
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Tbt-substituted 9-stannaphenanthrene was reported in 2005. At room temperature it forms the
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group and the even larger 2,4,6-trisphenyl or Tbt group. The two Sn-C bonds have
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6-membered aromatic rings with one carbon replaced by another group:
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Except where otherwise noted, data are given for materials in their
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InChI=1S/C5H5.Sn.H/c1-3-5-4-2;;/h1-5H;;/b3-1?,5-4-;;
441:Tbt-substituted stannabenzene synthesis. Reagents
608:Generation of Stannabenzenes and Their Properties
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373:atom. Stannabenzene itself has been studied by
357:Sn) is the parent representative of a group of
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556:Journal of the American Chemical Society
528:Journal of Molecular Structure: THEOCHEM
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415:A stable 2-stannanaphthalene derivative
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229:Key: USOBSXNBGFXQQW-RJPIHQCFSA-N
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381:Stable derivatives of stannabenzene
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644:Hypothetical chemical compounds
308:(at 25 °C , 100 kPa).
540:10.1016/j.theochem.2009.10.038
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377:, but has not been isolated.
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443:lithium aluminium hydride
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597:10.1246/cl.2005.1088
361:that are related to
65:Preferred IUPAC name
394:of 202.9 and 208.1
369:atom replaced by a
359:organotin compounds
298: g·mol
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639:Six-membered rings
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335:Infobox references
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649:Tin(IV) compounds
616:10.1021/om100382n
568:10.1021/ja057531d
477:, stannabenzene,
343:Chemical compound
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182:CompTox Dashboard
125:Interactive image
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634:Tin heterocycles
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507:telluropyrylium
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534:(1–3): 47–52.
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503:selenopyrylium
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17:Stannabenzene
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562:(4): 1050–1.
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499:thiopyrylium
491:bismabenzene
475:germabenzene
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400:double bonds
392:bond lengths
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84:Identifiers
76:Other names
487:arsabenzene
483:phosphorine
471:silabenzene
467:borabenzene
423:cycloadduct
259:Properties
628:Categories
513:References
449:(step 3),
445:(step 2),
388:tert-butyl
291:Molar mass
250:1=CC=CC=C1
136:ChemSpider
112:3D model (
91:CAS Number
453:(step 4)
576:16433501
495:pyrylium
479:pyridine
460:See also
430:DA dimer
404:aromatic
145:20137777
101:289-78-1
69:Stannine
365:with a
363:benzene
328:what is
326: (
296:184.813
157:PubChem
78:Stannin
574:
367:carbon
323:verify
320:
243:SMILES
170:119197
59:Names
218:InChI
114:JSmol
572:PMID
612:doi
593:doi
564:doi
560:128
536:doi
532:941
451:LDA
447:NBS
371:tin
187:EPA
160:CID
630::
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396:pm
349:(C
284:Sn
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355:6
353:H
351:5
318:N
281:6
278:H
275:5
272:C
189:)
185:(
116:)
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