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TABLE OF CONTENTS

Volume 21 Issue 7 , Pages 475 - 611 (July 2007)

Special Issue: Special issue dedicated to the memory of Des Cunningham International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead ICCOC-GTL-12


Contents

Contents (p i-v)

Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1297

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Editorial

Editorial (p 475)
Patrick McArdle,ieran Molloy
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1249

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Main Group Metal Compounds

Supramolecular aspects of tin and lead chemistry (p 476-482)
Ionel Haiduc
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1274

 

Supramolecular self-assembly through hydrogen bonds, dative (coordinate) bonds, soft-soft (secondary bond) and pi-bond interactions as bonding motifs available for supramolecular self-assembly in organotin and organolead chemistry is illustrated.

 

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Organotin compounds containing four-membered distannoxane [Sn(µ-OH)]2 units (p 483-503)
Vadapalli Chandrasekhar, Puja Singh,andasamy Gopal
Published Online: May 18 2007 4:51AM
DOI: 10.1002/aoc.1260

 

Compounds containing the distannoxane core [Sn2(µ-OH)2] are reviewed. Synthesis and structural aspects of these compounds are summarized in this article.

 

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Catalytic properties of cross-linked polystyrene grafted diorganotins in a model transesterification and the ring-opening polymerization of epsiv-caprolactone (p 504-513)
Kevin Poelmans, Vanja Pinoie, Ingrid Verbruggen, Monique Biesemans, Guy Van Assche, Gaëlle Deshayes, Philippe Degée, Philippe Dubois, Rudolph Willem
Published Online: May 23 2007 4:49AM
DOI: 10.1002/aoc.1259

 

The catalytic properties of a cross-linked poly- styrene-grafted diorganotin dichloride and chlorodistannoxane are compared in the transesterification reaction of ethyl acetate and n-octanol, as well as in the ring-opening polymerization (ROP) of -caprolactone. Moreover, 119Sn hr-MAS NMR and 117Sn CP-MAS NMR spectroscopy appear to be complementary techniques for the assessment of the tin(IV) functionality of the grafted tetraalkyldichlorodistannoxane showing a dimeric ladder arrangement.

 

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Alkynylorganotins, versatile precursors of class II hybrid materials (p 514-520)
Thierry Toupance, Mervyn de Borniol, Hicham El Hamzaoui, Bernard Jousseaume
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1272

 

Hydrolysis of ,-bis(trialkynyltin) compounds in which the two tin atoms are bridged through a rigid or a semi-rigid linker provides self-assembled tin-based hybrid materials. Calcination of these materials leads to nanocrystalline tin dioxide materials showing, in some cases, an unusual polymodal distribution of mesopore sizes.

 

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Synthesis and characterization of alpha, omega-bis [tri - (w - triphenylstannyl) butylstannyl] alkanes as starting materials for organotin dendrimers (p 521-530)
Yilmaz Aksu, Sevil Aksu, Herbert Schumann
Published Online: May 24 2007 11:32AM
DOI: 10.1002/aoc.1251

 

Alkylation of Cl3Sn(CH2)nSnCl3 (n = 4, 5) with BrMg(CH2)2CH2 affords (CH22CH2)3Sn(CH2)nSn(CH2CH2CH2)3, which undergoes hydrostannylation with Ph3SnH forming [Ph3Sn(CH2)4]3 Sn(CH2)nSn[(CH2)4SnPh3]3. Both com- pounds are converted by HCl to [ClPh2Sn(CH2)4]3Sn(CH2)nSn[(CH2)4SnPh2Cl]3, then by LiAlH4 to [HPh2Sn(CH2)4]3Sn(CH2)nSn[(CH2)4SnPh2H]3 and finally by CH22OH yielding [HO(CH2)3Ph2Sn(CH2)4]3Sn(CH2)nSn[(CH2)4SnPh2(CH2)3 OH]3.

 

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First 1,1-organoboration reactions of vinyltin compounds - a route to boryl-substituted stannolanes and organo-substituted stannol-3-enes (p 531-538)
Bernd Wrackmeyer, Oleg L. Tok
Published Online: May 18 2007 4:49AM
DOI: 10.1002/aoc.1263

 

Dimethyl(divinyl)tin reacts with trior- ganoboranes BR3 by intermolecular 1,1-organoboration, followed by ring closure via intramolecular 1,1-organoboration to give boryl-substituted stannolanes. With diethylborane hydroboration takes place, also followed by ring closure via cleavage of the SnC, and the mechanism was confirmed using di-2-propenyltin compounds.

 

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Synthesis and spectroscopic characterization of dimethyl/di(n-butyl)tin(IV)bis(O,Oprime-ditolyl dithiophosphate) complexes. Crystal structures of Me2Sn[S2P(OC6H4Me-o)2]2 and n-Bu2Sn[S2P(OC6H4Me-o)2]2 (p 539-544)
John E. Drake, Chitra Gurnani, Michael B. Hursthouse, Mark E. Light, Manisha Nirwan, Raju Ratnani
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1265

 

Organotin(IV) complexes of the type, R2Sn[S2P(OR)2]2 (where R = Me, Bu and R = o-, m-, p-C6H4Me) were obtained by the reaction of Me2SnCl2 or Bu2SnCl2 with ammonium salts of the corresponding O, O-ditolyl dithiophosphates. Crystal structures for Me2Sn[S2P(OC6H4Me-o)2]2 and Bu2Sn[S2P(OC6H4Me-o)2]2 were determined. The geometry around the tin atom in both molecules may be described as having skew-trapezoid bipyramidal geometry.

 

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Synthesis, larvicidal, QSAR and structural studies of some triorganotin 2,2,3,3-tetramethylcyclopropanecarboxylates (p 545-550)
Xueqing Song, Alejandra Zapata, Jana Hoerner, Angel C. de Dios, Leah Casabianca, George Eng
Published Online: May 18 2007 4:54AM
DOI: 10.1002/aoc.1241

 

A series of triorganotin 2,2,3,3- tetramethylcyclopropanecarboxy- lates, where R = methyl, ethyl, n-propyl, n-butyl, phenyl and cyclohexyl, have been synthesized. Based on the spectroscopic results, all the complexes, with the exception of the tricyclohexyl compound, were found to be five-coordinated, while the tri-cyclohexyltin derivative was determined to be four-coordinated in the solid state. NMR studies indicate that all the complexes are four-coordinated in solution. Larvicidal results indicated that this series of triorganotins are effective against three species of mosquito larvae. In addition, quantitative structure-activity relationships (QSARs) were also developed for each species of larvae.

 

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New stable germylenes, stannylenes, and related compounds. 8. Amidogermanium(II) and -tin(II) chlorides R2N-E14-Cl (E14 = Ge, R = Et; E14 = Sn, R = Me) revealing new structural motifs (p 551-556)
Victor N.hrustalev, Ivan V. Glukhov, Irina V. Borisova, Nikolay N. Zemlyansky
Published Online: May 23 2007 4:47AM
DOI: 10.1002/aoc.1252

 

New stable amidogermanium(II) and -tin(II) chlorides R2NE14Cl [E14 = Ge, R = Et (1), E14 = Sn, R = Me (2)] have been synthesized and their crystal structures have been determined by X-ray diffraction analysis. Both structures of 1 and 2 represent new structural motifs for amidogermanium(II) and -tin(II) chlorides, respectively. The electronic structures of 1 and 2 were studied using the DFT.

 

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Synthesis of novel stereodefined vinylgermanes bearing an allyl group or an allenyl group: (E)-2-aryl-1-germylalka-1,4-dienes and (E)-4-aryl-5-germylpenta-1,2,4-trienes (p 557-571)
Kotaroato, Yoshiya Senda, Yoshiaki Makihara, Takeshiojima, Hiroyukiurihara, Yutaka Takahashi, Taichi Nakano
Published Online: May 23 2007 4:44AM
DOI: 10.1002/aoc.1264

 

Stereodefined synthesis of an unprecede- nted family of vinylgermanes bearing an allyl group, (E)-2-aryl-1-germylalka-1,4-dienes, or an allenyl group, (E)-4-aryl-5-germylpenta-1,2,4-trienes, via a cross-coupling reaction of (Z)-germyl(stannyl) ethenes with the respective allyl halide (Br, Cl) and propargyl bromide is described.

 

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The development of a lsquosafety-catchrsquo arylgermane for biaryl synthesis by palladium-catalysed germyl-stille cross-coupling (p 572-589)
Alan C. Spivey, Christopher J. G. Gripton, Joseph P. Hannah, Chih-Chung Tseng, Paul de Fraine, Nigel J. Parr, Jan J. Scicinski
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1270

 

Bis(2-naphthylmethyl)aryl germane 18b is identified as a safety-catch precursor for Pd(0) catalysed cross-coupling with aryl bromides activated by TBAF in DMF. The 2-naphthylmethyl substituents are removed via photolytic oxidation in the presence of Cu(BF4)2.

 

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Hydrosilylation of unsaturated fatty acid N-phenyl amides (p 590-594)
A. Eladib, N.atir, A. Castel, F. Delpech, P. Rivière
Published Online: May 25 2007 9:39AM
DOI: 10.1002/aoc.1240

 

New silylated fatty acid N-phenyl amides have been synthesized and characterized. According the position of the double bond (terminal or internal), hydrosilylation reactions were performed using transition metal catalysis or radical initiation sequence.

 

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Synthesis and structures of M(Me3SiNCHNSiMe3)3 (M = Al, Ga) via reactions of M-hydrides with Me3SiNCNSiMe3 (p 595-600)
Cole Ritter, Andrew V. G. Chizmeshya, T. L. Gray, J.ouvetakis
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1277

 

The hexacoordinate M(Me3SiNCHNSi- Me3)3 (M = Al,Ga) metal amidinate compounds incorporating the bidentate [Me3 SiNCHNSiMe3]1- ligand were synthesized for the first time. X-ray diffraction revealed molecular structures in which the amidinate groups form three MNCN propeller paddles terminated by six SiMe3 groups, surrounding the central metal atom. The AlNCN ring and the two corresponding Si atoms lie virtually on the same plane within each propeller unit.

 

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(3-Aminopropyl)trifluorosilanes and their N-substituted derivatives (p 601-603)
Mikhail G. Voronkov, Nikolai F. Chernov, Aleksander I. Albanov, Olga M. Trofimova, Yulya I. Bolgova, Ekaterina A. Grebneva
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1271

 

N-substituted (3-aminopropyl)trifluorosilanes RRNCH2CH2CH2SiF3 were synthesized in order to investigate the effect of the substituents at the nitrogen atom on the NSi intramolecular interaction. Compounds were prepared by the reaction ofF with F3BN(CH2CH2CH2SiF3)RR or H(RRNCH2CH2CH2SiF4). The structure of the compounds was confirmed by 1H, 13C, 19F, 29Si NMR and IR spectroscopy. The spectral data suggest pentacoordination at silicon in the compounds with R = R = H, Me resulting from a relatively strong N Si intramolecular bonding.

 

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Synthesis and reactions of a novel bulky aryllithium (p 604-611)
Masaichi Saito, Yuta Okuyama, Tomoyuki Tajima, Daichiato, Michikazu Yoshioka
Published Online: Jun 14 2007 6:05AM
DOI: 10.1002/aoc.1268

 

A novel bulky aryllithium, 2,6-bis{2, 5-bis[bis(trimethylsilyl)methyl]phenyl}pheny- llithium (BbspLi), was synthesized. Reactions of BbspLi 5 with Group 14 electrophiles such as stannous chloride with carbon tetrachloride or tetrachlorometallanes gave fluorene 6. Reaction of BbspLi with carbon tetrachloride gave benzyl chloride 8, which converted to 6 under acidic conditions. Thus, BbspLi 5 isomerized to the corresponding benzyl anion 10, which underwent halophilic reactions with Group 14 electrophiles to give fluorene 6 via the benzyl chloride intermediate 8.

 

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