358:
105:
25:
96:
182:, though the former may yield the ether complex of the product. However, unlike that of gallium and indium, trialkyl thallium compounds cannot be prepared from dialkyl mercury and thallium trihalides, in which case R
568:
Niemeyer, Mark; Power, Philip P. (1998). "Synthesis and Solid-State
Structure of 2,6-Trip2C6H3Tl (Trip=2,4,6-iPr3C6H2): A Monomeric Arylthallium(I) Compound with a Singly Coordinated Thallium Atom".
341:
in nature. Nucleophile treatment can displace the halide atom, and substituent self-exchange to form thallium(III) halides and diphenylthallium halides is also possible. The dichloride can undergo
77:
bond. The area is not well developed because of the lack of applications and the high toxicity of thallium. The behavior of organothallium compounds can be inferred from that of
233:
TlOH is strongly basic. The structure of the dialkyl thallium anion resembles that of dialkyl mercury. However, dimeric or polymeric structures may exist in inert solvents or
494:
Wright, Robert J.; Phillips, Andrew D.; Hino, Shirley; Power, Philip P. (2005). "Synthesis and
Reactivity of Dimeric Ar'TlTlAr' and Trimeric (Ar' 'Tl)
281:
TlBr can act as alkyl donors for low-valent metal halides, performing oxidative alkyl insertions onto the metals with itself being reduced to
696:
667:
630:
478:
581:
249:, or the reaction of trialkylthallium compounds with protonic compounds. Another preparation involves the oxidation of thallium metal with
46:
856:
728:
136:
Organothallium(I) compounds remain obscure and limited scope. Attempts to generate the simple compound thallium methyl results in
498:(Ar', Ar' ' = Bulky Terphenyl Group) Thallium(I) Derivatives: Tl(I)βTl(I) Bonding in Species Ligated by Monodentate Ligands".
421:
The first organothallium compound, diethylthallium chloride, was prepared in 1870, shortly after the discovery of the element
140:, giving thallium(III) derivatives. With the bulky tris(trimethylsilyl)methyl substituent, a tetramer has been crystallized.
369:
154:, with cyclopentadiene. Thallium(I) cyclopentadienide adopts a zig-zag chain structure of cyclopentadienide and thallium.
541:]βAn Alkylthallium(<SCP>I</SCP>) Compound with a Distorted Tetrahedron of Tl Atoms in the Solid State".
413:
The resulting aryl thallium compounds react with nucleophiles such as halides, pseudohalides, and certain acetylides.
337:, with the tendency increasing from chlorine to iodine, to the point that the iodide derivative is unknown. They are
372:
with arenes. Moreso than Hg(II), thallium(III) is a potent electrophile, delivering arylthallium(III) derivatives:
147:
449:
261:
Dialkyl
Organothallium Compounds are mostly stable to air and moisture. The halide atom can be substituted by
434:
322:
253:
salts. They are formed from dialkyl mercury and thallium trihalides instead of trialkyl thallium compounds.
174:
Trialkyl thallium compounds, like those of indium and gallium, can be prepared from thallium trihalides and
78:
309:. Excess boronic acid will result in diarylthallium chloride formation. Thallium(III) trifluoroacetate can
439:
82:
179:
171:
and planar. In the solid phase, there is significant intermolecular interactions between the monomers.
812:
346:
299:
533:
Uhl, Werner; Keimling, Sven Uwe; Klinkhammer, Karl
Wilhelm; Schwarz, Wolfgang (1997). "Tl[C(SiMe
282:
266:
250:
195:
137:
832:
766:
724:
692:
688:
663:
626:
515:
474:
365:
234:
245:
Dialkyl
Organothallium Halides can be prepared from two equivalents of Grignard reagents and
85:
compounds. Organothallium(III) compounds are more numerous than organothallium(I) compounds.
824:
793:
758:
577:
550:
507:
342:
246:
214:
175:
151:
210:
357:
850:
338:
191:
306:
201:
Trialkyl thallium compounds can undergo alkyl exchange with itself and some acidic
622:
334:
262:
202:
187:
582:
10.1002/(SICI)1521-3773(19980518)37:9<1277::AID-ANIE1277>3.3.CO;2-T
143:
Similarly, thallium(I) aryl compounds require steric bulk for their isolation.
104:
836:
797:
770:
321:. Alkenes can also react with thallium(III) salts in a fashion analogous to
554:
519:
750:
828:
762:
720:
444:
422:
74:
95:
784:
Taylor; Kienzle, Frank; McKillop, Alexander (1976). "2-Iodo-p-Xylene".
310:
168:
511:
229:
TlX has ionic properties, such that they are water soluble and that R
206:
70:
167:
In the gas and liquid phase, trialkyl organothallium compounds are
356:
103:
94:
44:
parameter to this template to explain the issue with the article.
597:
Organometallic
Syntheses, Volume 2 Nontransition-Metal Compounds
364:
The most prominent contribution of organothallium chemistry to
186:
TlX will be obtained. Trimethyl thallium can be prepared from
18:
150:. It arises by treatment of thallium(I) salts, such as
749:Challenger, Frederick; Richards, Oswald V. (1934).
543:Angewandte Chemie International Edition in English
333:Phenylthallium dihalides are prone to eliminating
751:"94. Organo-derivatives of bismuth and thallium"
198:. Triethyl thallium can be similarly prepared.
325:to yield monoalkyl organothallium compounds.
298:Arylthallium dichloride can be prepared from
8:
265:, and the alkyl group can be abstracted by
34:needs attention from an expert in Chemistry
146:A well-known organothallium(I) species is
755:Journal of the Chemical Society (Resumed)
500:Journal of the American Chemical Society
406:
402:
398:
394:
390:
386:
382:
378:
570:Angewandte Chemie International Edition
461:
213:. Some trialkyl thallium compounds are
744:
742:
740:
49:may be able to help recruit an expert.
595:J. J. Eisch, R. B. King, ed. (1981).
7:
710:
708:
650:
648:
646:
644:
642:
612:
610:
608:
606:
16:Organometallic compounds of thallium
817:Quarterly Reviews, Chemical Society
289:Monoalkyl Organothallium Compounds
14:
313:aromatic rings to form ArTl(OCOCF
163:Trialkyl Organothallium Compounds
221:Dialkyl Organothallium Compounds
23:
251:aryldiazonium tetrafluoroborate
69:are compounds that contain the
683:Housecroft, Catherine (2018).
617:Housecroft, Catherine (2018).
370:thallium(III) trifluoroacetate
1:
158:Organothallium(III) Chemistry
660:Books of Inorganic Chemistry
89:Organothallium(I) Chemistry
873:
813:"Organothallium chemistry"
148:thallium cyclopentadienide
132:. Color code: magenta= Tl.
108:Structure of trimeric Tl(C
811:Lee, A. G. (1970-01-01).
717:Chemistry of the Elements
662:]. pp. 524β528.
473:. VCH. pp. 126β128.
469:C. Elschenbroich (2006).
857:Organothallium compounds
798:10.15227/orgsyn.055.0070
450:Organometallic chemistry
67:Organothallium compounds
435:Organogallium chemistry
555:10.1002/anie.199700641
440:Organoindium chemistry
361:
235:crystalline structures
180:organolithium reagents
133:
99:
792:: 70first1=Edward C.
360:
107:
98:
47:WikiProject Chemistry
829:10.1039/QR9702400310
763:10.1039/jr9340000405
723:. pp. 262β265.
691:. pp. 887β892.
625:. pp. 887β892.
685:Inorganic Chemistry
619:Inorganic Chemistry
283:thallium(I) bromide
247:thallium trihalides
715:Greenwood (2001).
362:
307:aryl boronic acids
196:thallium(I) iodide
138:disproportionation
134:
100:
786:Organic Syntheses
698:978-1-292-13414-7
669:978-7-03-056380-4
632:978-1-292-13414-7
599:. Academic Press.
512:10.1021/ja0432259
506:(13): 4794β4799.
480:978-3-527-29390-2
366:organic synthesis
347:mercuric chloride
176:Grignard reagents
64:
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719:(2nd ed.).
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687:(5th ed.).
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621:(5th ed.).
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576:(9): 1277β1279.
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353:Aryl derivatives
343:transmetallation
152:thallium sulfate
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36:. Please add a
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823:(2): 310β329.
803:
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729:
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549:(1β2): 64β65.
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192:methyl lithium
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188:methyl iodide
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79:organogallium
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32:This article
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377:ArH + Tl(O
363:
339:Lewis acidic
332:
297:
263:nucleophiles
260:
244:
224:
203:hydrocarbons
200:
173:
166:
145:
142:
135:
83:organoindium
66:
65:
52:
41:
37:
33:
757:: 405β411.
368:centers on
335:halobenzene
294:Preparation
241:Preparation
656:ζ ζΊεε¦δΈδΉ¦ 第δΊε·
456:References
389:β ArTl(O
837:0009-2681
771:0368-1769
329:Reactions
257:Reactions
169:monomeric
55:June 2024
851:Category
721:Elsevier
520:15796545
445:Thallium
429:See also
423:thallium
75:thallium
689:Pearson
623:Pearson
417:History
311:oxidize
207:alkynes
124:-2,6-Me
116:-2,6-(C
835:
769:
727:
695:
666:
629:
518:
477:
194:, and
71:carbon
38:reason
658:[
401:+ HO
345:with
205:like
40:or a
833:ISSN
767:ISSN
725:ISBN
693:ISBN
664:ISBN
627:ISBN
516:PMID
475:ISBN
305:and
300:TlCl
269:. (C
209:and
81:and
42:talk
825:doi
794:doi
759:doi
578:doi
551:doi
508:doi
504:127
405:CCF
393:CCF
381:CCF
178:or
853::
831:.
821:24
819:.
815:.
790:55
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765:.
753:.
739:^
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547:36
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796::
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761::
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580::
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275:6
273:F
271:5
231:2
227:2
225:R
184:2
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126:2
122:3
120:H
118:6
114:3
112:H
110:6
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53:(
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