Indian Journal of Chemistry Vol. 41B. March 2002. pp. 608-613

Synthesis and characterization of new l-organy lsilatranes

Shailesh C Verma & M Nasim*

Defence Materials & Stores Research & Development Establishment. DMSRDE PO. G T Road. Kanpur 208013. India

Received 11 August 2000; accepted (re vised) 9 October 2001

A series of I-organyl- and l -organyl-3.7.1O-trimethylsilatranes. Rii(OCHRICH2h~. where RI = H or CH] and R = CH]CONH(CH2h-. H2NCONH(CH2h-. CJ190(CH2h-. C]HsN2(CH2h-. and C]N]0 3(CH2h- have been synthesized in high yields ranging from 82 to 95% by transetherification of the corresponding I-organyltrialkoxysilanes with trialkanolamines i.e. triethanolamine and triisopropanolamine. These new silatranes have been well characterized by elemental analyses. IR. I Hand I3C NMR spectroscopy .

The much studied pentacoordinated silicon com­pounds known as silatranes, (l-organyl-2,8,9-trioxa-5-aza-I-silatricyclo[3,3,3,01.5]undecanes) include some compounds that have carbo-functional substituents on the si licon atom and these are of special interest in respect of their structure, reactivity and biological activi ty l.2 . Yoronkov has reported that LD50 values of silatranes depend on the cage structure3. Synthesis of new silatranes are of much interest in view of their interesting biological activitl-5, physicochemicaI6-9, and structural properties ,o. '7 . Chemical investigations of these hypervalent silicon species are being inten-. I d '8-2o slve y pursue .

The potential applications of silatranes as rodenti­cides21 , insecticides5, crop yield enhancement3

,22,

medicines2,3, agrochernicals23.25 , polymer and com­

posite materials2,26,27, water and oil repellent in tex­tiles2, corrosion inhibitor2,28,29, sericulture (silk pro­duction)3,3o, and as single source precursor for MOCYD31 ,32 as well as our own interest in the field of silatranes I5,16,27,3346 prompted us to undertake the syn­thesis and characterization of new I-organylsilatranes , We have initiated work in this direction and in this paper we now report the preparation and spectro­scopic investigations of a series of l-organyl- and 1-organyl-3,7.10-trimethylsi latranes.

Results and Discussion Transetherification of l-organyltrialkoxysilanes

(1 -5) with trialkanolamines (6 or 7), gave silatranes la-Sa or lb-Sb, respectively, in yields 82-95% in ac­cordance with Scheme I. The compounds 2b, 3b and 4b were purified by vacuum distillation while the pure compounds la, 3a-Sa, lb and Sb were obtained as a solid and purified by recrystallization from ch lo-

rofonn and pet. ether (b.p. 40-60°C). All the com­pounds were well characterized by elemental analy­ses, IR, 'H and I3C NMR. The 'H and I3C NMR spec­tra of compound 2a could not be recorded due to in­soluble nature of the compound. However, IR spectra confirmed the proposed structure of compound 2a , Satisfactory elemental analyses of this compound were also obtained. Melting point, IR and elemental analyses of compound 2a was carried out without pu­rification,

Infrared spectra: Absorption frequencies of bonds of l-organylsilatranes (la-Sa) and l-organyl-3,7,1O­trimethyl si latranes (lb-Sb) observed in the lR spectra fully substantiate the structures. The structural frag­ment of Si-O-C-C of silatrane skeleton is character­ized by the typical frequencies appearing at 979-940, 1023- 10 I 0 cm-I and a group of split bands in the re­gion at 1114-1085 cm·1 47 , The characteristic spectra of a pentacoordinated molecular structure were ob­served as medium intensity band at 586-570 cm· 1 as­signed to the bending vibration of silatrane skeleton as well as stretching vibration of the Sif-N coordina­tive bond indicating the coordination from nitrogen to silicon38

,48.49, The other absorption characteri stics of

the group appeared at 2975-2969 (va.,CH3), 2879-2868 (VsCH3)50, 1463-1440 and 1379-1372 cm·1 (oCHrC) for C-CH3 group. The characteristic absorption fre­quencies of si latrane skeleton and side groups for compounds la-Sa and lb-Sb are cited in the text.

IH NMR spectra: In the 'H NMR spectra the sig­nals of the NCH2 and OCH2 proton of the silatranyl fragment of la-Sa appeared as triplet at 8 2,71-2,87 and 8 3.61-3.87 ppm, respectively. The 'H NMR spectra of the compounds lb-Sb are extremely

VERMA el al. : SYNTHESIS OF NEW l -ORGANYLSILATRANES 609

hR'

00 (RObSi (CH:1lnX

1 - 4 R1= H (6), Me (7)

1/ x(CH~n-S\y

R = Et, n = 3 , X= -NHCOCH3 (1)

R = Me, n = 3, X= -.NHCONH 2 (2)

R = Me, n = 2 , X = --0 (3)

o

R=Et , n=3,X=-N~ (4)

R' 1 a - 5a and 1 b - 5b

R1 = H, n = 3, X ~ -NHCOCH3 (la)

R1 = Me, n = 3, X = -NHCOCH3(lb)

R1 = H, n = 3, X = -NHCONH2 (2a)

R1 = Me, n = 3, X = -NHCONH2(2b)

R1 = H, n = 2, X =-q (3a)

o R1 =Me,n=2'X~ (3b)

o

R1 = H,n=3 , X=-N~ (4a)

R1 = Me, n = 3, X =-N~ (4b)

o 6 or 7 Sil-NAN-Sil

----------.. odlN)bo I Sil

5 R' R' = - (CH2b Si(OMeb

7 R' 80 9' 6

1/ /0 11

o 4 2 3

R'

R1 = H (5a) , Me (5b)

Scheme I

complex due to the asymmetry of the methyl substituted carbon atoms in the atrane fragment which results in the nonequivalence of the protons of this moiety and also because of clear evidence of the presence of two diastereomers in C-substituted silarranes51

. Therefore, these are nor easily amenable to interpretation and clear-cut assignment of methyl, NCH2, -OCH (atrane fragment protons) and orher

protons. The methyl protons, NCH2 and -OCH protons of the atrane moiety were enveloped in a complex mu ltiplet at 8 0.99-1.26, 2.09-3.03 and 3.60-4.10 ppm, respectively .

I3C NMR spectra: I3C NMR spectroscopy is more informative for C-substituted atranes52

. The trialka­nolamine signals appeared in characteristic positi ons for silatrane derivatives53

. The triisopropanolamino

610 INDIAN J. CHEM., SEC B, MARCH 2002

derivative contained RRRlSSS and RRS/SSR di­astereomers, the former having single l3C peaks for each carbon type, while the latter, being less symmet­rical, exhibited separate signals for each of the NCH2, -OCH and CH3 carbon of the triisopropanolamine cage. So carbon atoms of NCH2 and -OCH gave 8 signals in the range between 8 58.43-67.39 ppm while carbon atom of CH3 gave 4 signals in the range be­tween 820.01-23.41 ppm.

Experimental Section

General. Melting points al1d boiling points are un­corrected. Melting points were taken on a Toshniwal melting point apparatus. All the operations were car­ried out under argon atmosphere. IR spectra were re­corded using KBr discs and nujolmull (vmax in cm- ') in the range 4000-400 cm-' on a Nicolet Magna 750 FfIR spectrophotometer. 'H and '3C NMR spectra were recorded on Jeol 90 FX (90 MHz) and Brucker DPX 300 (300 MHz) instruments in CDCl3 or C6D6 with TMS as internal standard . Chemical shifts are quoted in ppm down field from TMS. C, Hand N analyses were carried out on Elemental analyser sys­tem GmbH analyser, Vario EL.

Triethanolamine 6 (Ranbaxy) distilled prior to use. Triisopropanolamine 7 (Fluka) and l-organyltrialk-0xysilanes i.e. N-[3-(trimethoxysilyl)propyl]urea 2 (Aldrich), 2-[(3,4-epoxycyclohexyl)ethyl]trimethoxy­silane 3 (Fluka), 1-[3-(triethoxysilyl)propyl]-2-imida­zoline 4 (Fluka), tris-[3-(trimethoxysilyl)propyl]iso­cyanurate 5 (Aldrich) were used as supplied. N-[3-(triethoxysilyl)propyl]acetamide 1 was prepared as described in the literature54

. Reagent grade solvents were dried and purified by conventional methods. Pet. ether (b.p. 40-60°C) was distilled and dried over so­dium wire immediately before use.

Synthesis of N-[3-(triethoxysilyl)propyl]aceta­mide 1. A mixture of 3-aminopropyltriethoxysilane (l5.47g, 70 mmole) and acetamide (4. 13g, 70 mmole) in presence of catalytic amount of ammonium sul­phate was heated to refl ux for 18 hr at ISO-60°C and distilled in vaccuo. The yield of compound 1 obtained was 16.5g (90%); b.p. 196-98°C/6mm of Hg. Anal. Found: C, 50.33; H, 9.73; N, 5.23; Si , 24.13. Calcd for C 1,H25N04Si: C, 50.15; H, 9.57; N, 5.32; Si , 24.30%. IR (nujol): 3293br (vasNH), 3089s (vsNH), 2975vs (v""CH3), 2930vs (vasCH2), 2887vs (vsCH2,

vsCH3), 1656vs (vC=O), l558s (8NH), 1479w, 1442s, 1388s, 1371 s (8C-CH3), 1293s (wCH20), 1194s (-cCH20), I 166vs, 1116vs, 1078vs, 957s (vSi-O-C-C),

882w (vC-N), 791vs (vasSi-O), 703w, 682w and 602s (vsSi-O) cm-'; 'H NMR (8, CDC]3): 0.61 (t, 2H, CH2Si, J=6.75 Hz), 1.23 (t, 3H, CH3C, J=6.39 Hz), 1.60 (m, 2H, CCH2C), 1.94 (s, 3H, COCH3), 3.22 (m, 2H, NCHrC), 3.87 (q, 2H, OCH2), 6.55 (s, 1 H, NH).

General synthetic procedure for l-organyl­silatranes (la-Sa) and (lb-5b). The reactions were conducted in a three necked round bottom flask fitted with a dropping funnel and reflux condenser and mounted on a magnetic stirrer. Trialkanolarnine (6 or 7) and catalytic amount of KOH were taken in solvent (benzene or toluene), and to this equimolar amount of corresponding silanes taken in solvent was added dropwise during 15 min with constant stirring at room temperature. The solution was heated to reflux. The alcohol formed during course of the reaction was dis­tilled off and reaction mixture was concentrated by removal of solvent. The products were purified by recrystallization or by vacuum distillation.

N -[3-(silatranyl)propyl]acetamide 1a. Compound 1a was obtained by stirring and refluxing a solution of compound 1 (2.63g, 10 mmole) and compound 6 (1.49g, 10 mmole) in 50 rnL benz~ne containing KOH as catalyst for 3 hr, yield 2.33g (85%); m.p.140-41 dc. Anal. Found: C, 48.39; H, 7.73; N, 10.23; Si, 10.43. Calcd for C ll H22N20 4Si: C, 48 .15; H, 8.08; N, 10.12; Si, 10.13%. IR (KBr): 3212s (vasNH), 3088s (vsNH), 2970vs (vasCH3), 2878s (vsCH3), 1665vs (vC=O), 1550m (8NH), l439s, 1381 m (8CH3C), 1340w (wCH2N), 1279m (wCH20), 1190w (-cCH20), ll17vs, 1091 vs (vC-O), 1050w, 1022s (vasNC3), 943m (vC­C), 915s (vsNC3), 880w (vC-N), 783s, 760s (vasSi-O), 717m, 680w, 625m (vsSi-O), 585m (Sif-N) em-i; 'H NMR (8, CDCI3): 0.42 (t, 2H, SiCH2), 1.62 (m, 2H, CCH2C), 1.95 (s, 3H, CH3), 2.81 (t, 6H, NCH2), 3.24 (t, 2H, CH2N), 3.87 (t, 6H, OCH2), 6.65 (s, IH, NH); l3C NMR (8, CDCI3) : 11.60 (SiCl'h), 23.70 (CH3),

24.30 (CG-I2C), 44.3 (CH2N), 51.0 (NCH2), 57 .70 (OCH2), 171.30 (C=O).

N-[3-(3,7,10-trimethylsilatranyl)propyl]acetamide lb. Compound Ib was obtained by stirring and refluxing a solution of compound I (2.63g, 10 mmole) and compound 7 (1.91g, 10 mmole) in 50 rnL benzene containing KOH as catalyst for 3 hr, yield 2.56g (82%); m_p. 123-24°C. Anal. Found: C, 53 .39; H, 8.63; N, 9.23; Si , 9.23. Calcd for C'4H2sN20 4Si : C, 53.14; H, 8.92; N, 8.85; Si, 8.87%. IR (KBr): 3296s (vasNH), 3094s (vsNH), 2975vs (vasCH3), 2879s (vsCH3), 1636vs (vC=O), l559m (8NH), 1440s, 1372 (8CH3C), 1330vw (wCH2N), 1285m (wCH20),

VERMAet al.: SYNTHESIS OF NEW l-ORGANYLSILATRANES 611

1197w ('tCH20), 1121 VS, 1l09vs (vC-O), 1060vs,

1023vs (vasNC3), 970s (vC-C), 920w (vsNC3), 880w

(vC-N), 780s, 760s (VasSi-O), 715m, 680w, 625m (vsSi-O), 587m (Sit-N) cm·l; IH NMR (8, CDCI3): 0.53 (t, 2H, SiCH2), 1.05-1.21 (m, 9H, CH3), 1.48 (m, 2H, CCH2C), 2.0 1 (s, 3H, CH3), 2 .55-2.91 (m, 6H, NCH2), 3. 13 (t, 2H, CH2N), 3.75-3.99 (m, 3H, OCH), 6.81 (s, IH, NH); l3C NMR (8, CDCI3): 12.30 (SiCH2), 20.09, 20.21, 20.45, 23.01(CH3 -atrane), 23.20 (CH3), 25.10 (CCH2C), 42.70 (CH2N). 58.53, 61.33,62.65, 63 .75 , 64.48, 64.73, 65.38, 66.58 (OCH and NCH2), 170.60 (C=O).

N-[3-(silatranyl)propyl]urea 2a. Compound 2a was obtained by stirring and reflux ing a solution of compound 2 (22.23g, 100 mmole) and compound 6 (l4.9g, 100 mmole) containing KOH as catalyst for 1 hr. Precipitated white crystalline solid was washed with pet. ether and dried in vacuo, yield 25 .06g (9 1%); m.p. 195-97°C. Anal. Found: C , 43 .39; H, 7.43; N, 15.42; Si, 9.93. Ca1cd for C lOH21 N30 4Si : C, 43.62; H, 7 .69; N, 15.26; Si , 10.19%. IR (KBr): 3417s

(vasNH), 3336s (vsNH), 1630vs (vC=O), 1529m (8NH l° and 8NH2°), 1370m, 1335s (wCH2N), 1275m (wCH20), 1 I 83m ('tCH20 ), 11 20vs, 1085vs (vC-O),

1050vw, 1020s (vasNC3), 945s (vC-C), 910s (vsNC3), 880w (vC-N), 783s, 763vs (vasSi-O), 715s, 670vw, 615m (vsSi-O), 586 m (Sit-N) cm'l.

N-[3-(3,7,lO-trimethylsiiatrallyl)propyl]urea 2b. Compound 2b was obtained by stining and refiuxing a solution ()f compound 2 (22.23g, 100 mmole) and com­pound 7 (L'. lg, 100 mmole) in 100 rnL toluene contain­ing KOH as catalyst for 3 hr, yield 28.57g (90%); m.p. 56-58°C, b.p. 254-55°Cllmm of Hg. Anal. Found: C, 4939; H, 8.43; N, 13.42; Si, 8.24. Ca1cd for C 13H27N304Si: C, 49.1 8; H, 8.57; N, 13.24; Si, 8.84%. IR (KBr): 3425s (vasNH), 3359s (vsNH), 2970vs

(v",CH3), 2875vs (vsCH3), 1637vs (vC=O), 1568m (8NH 1° and oNH2°), 1461s, 1379m (8CH3C), i350m

(wCH2N), 1266m (wCH20), 1180w (TCI-fzO), 1158vs, 1110vs (vC-O), 1068vs, 1020s (vasNC3). 979vs (vC-C), 910vw (vsNC), 882s (vC-N), 774vs (va,Si-O), 725s, 670m, 615m (vsSi-O), 570m (Sit-N) cm· l

; IH ~'MR (0, CDCh): 0.30 (t, 2H, SiCH2), 0.99- 1.12 (m, 9H, CH3),

1.48 (m, 2H, CCH2C), 2.05-2.21 (t, 2H, CH2N), 2.52-2.99 (m, 6H, NCH2), 3.75-4.02 (m, 3H, OCH), 4.68 (s, 3H, NH and NH2); DC NMR (0, CDCl) : 12.97 (SieH2). 20.01,20.12.20.37, 22.90 (CH), 24.94 (CCH2C), 43.06 (CH2N), 58.43, 61.24, 62.95, 63.87, 64.50, 64.63, 65.14, 66.33, (OCH and NCH2), 158.57 (C=O).

2-[(3,4-EpoxycyciohexyJ)ethyl]silatrane 3a. Com­pound 3a was obtained by stirring and refluxing a solution of compound 3 (7.50g, 30 mmole) and com­pound 6 (4.50g, 30 mmoJe) in 50 rnL benzene con­taining KOH as catalyst for 2 hr, yield 8.08g (90%); m.p. liS- 17°C. Anal. Found: C , 56.39; H,8.63; N, 4.42 ; Si , 9.24. Calcd for C I4H2sN04S i: C, 56.l6; H, 8.42; N, 4.68 ; Si, 9.37%. IR (KBr): I 646m, 1547m

(epoxycyclohexane ring) , 1361m, 1340w (wCH2N),

1275s (CDCH20), 11 80m ('rCH20 ), 1130vs , l100vs

(vC-O), 1050vw, 1010s (vasNC3), 942s (vC-C), 911s

(vsNC3), 880s (vC-N), 780vs, 760vs (vasSi-O), 720s, 680vw, 619s (vsSi-O), 586m (Sit-N) cm' l; IH NMR

(0, CDCI3): 0.51 (t, 2H, SiCH2), 0.93-2.25 (m, 9H, epoxycyclohexane ring), 1.78 (m, 2H, CCH2C), 2.80 (t, 6H, NCH2), 3.81 (t, 6H, OCH2); l3C NMR (8, CDCl3): 12.80 (SiCH2), 25.0 (CCH2C), 26.32, 31.27, 35.41, 52.01 , 52.81, 53.33 (epoxycyclohexane ring), 51.20 (NCH2), 57.90 (OCH2).

2-[ (3,4-Epoxycyciohexyl)ethylJ-3, 7,1 O-trimethyl­silatrane 3b. Compound 3b was obtained by stirring and refluxing a solution of compound 3 (24.63g, 100 mmole) and compound 7 (l9.1g, 100 mmole) in 100 rnL toluene containing KOH as catalyst for 3 hr, yield 30.05g (88%); b.p. 208-10°CI2.5mm of Hg. Anal. Found: C, 59.49; H, 9.33; N, 4.42; Si, 8.34. Calcd for C I7H3I N04Si: C, 59.79; H, 9.15; N, 4.10; Si, 8.22%.

IR (nujol): 2970vs (VasCH3), 2869s (VsCH3), 1650w, 1542w (epoxycyclohexane ring), 1454s, 137601

(8CH3C), 1343m (CD CH2N), 1269m (CD CH20),

1180m ('rCH20), 1156vs, 1112vs (vC-O), 1067vs, 1013vs (vasNC3), 975vs (vC-C), 920w (vsNC3), 882s

(vC-N), 77lvs, 760s (vasSi-O), 728s, 680w, 656m (vsSi-O), 579 m (Si t-N) cm· l; 'H NMR (8, CDCl3): 0.30 (t, 2H, S:CH2), 1.05-1.14 (m, 9H, CH3), 1.58 (m, 2H, CCH2C), 0 .91-2.34 (m, 9H, epoxycyclohexane ring), 2.49-3 .03 (m, 6H, NCH2) , 3.72-4.06 (01, 3H, OCH); IJC NMR (0, CDCl): 13.10 (SiCH2), 20.01, 20.11, 20.44, 22.83 (CH3), 24.01 (CCH2C), 25 .34, 31.74, 35.44, 51.81, 52.56, 53 .10 (epoxycyclohexane ring), 58 .61, 61.37, 6 1.57, 63.08 , 64.67, 64.89, 66.57, 67.04 (OCH and NCH2).

1-[3-(Silatranyl)propyJ]-2-imidazoline 4a. Com­pound 43 as obtained by stirring and refiuxing a solution of compound 4 (l0.97g, 40 mmole) and compound 6 (5.97g, 40 mmole) in 50 mL benzene contai ning KOH as catalyst for 3 hr, yield 10.93g

(95%); m.p. 92-94°C. Anal. Found: C, 50.79; H, 8.35; N, 14.90; Si, 9 .72. Ca1cd for CI2H23N30 )Si: C, 50.50 ; H, 8.12; N, 14.72; Si, 9.83%. IR (KBr): 1660m,

612 INDIAN J. CHEM .• SEC B. MARCH 2002

1602m (imidazoline ring), 1368m, 1330vw (wCH2N), 1283m (wCH20), 1170w ('tCH20), 1125vs, 1096vs (vC-O), 1050vw, 1023s (VasNC3), 950s (vC-C), 917s (vsNC3), 880w (vC-N), 771 vs, 761 vs (vasSi ~O), 715m, 680w, 632m (vsSi-O), 585m (Si~N) cm" ; 'H NMR (8, CDCb): 0.38 (t, 2H, SiCH2), 1.60 (m, 2H, CCH2C), 2.81 (t, 6H, NCH2), 3.20 (t, 2H, CH2N), 3.77 (t, 6H, OCH2), 3.32 (t, 4H, CH2, 1=10.0 Hz) (imida­zoline ring), 6.75 (s, 1 H, CH); \3C NMR (8; CDCI3): 11-70 (SiCH2), 2520 (CCH2C), 41-70 (CH2N), 51-30 (NCH2), 57.70 (OCH2), 50.20 (C~5), 54.70 (C-4), 15730 (C-2) (imidazoline ring).

1-[3-(3,7,10-TrimethylsilatranyJ)propyJJ-2-imid­azoline 4b. Compound 4b was obtained by stirring and refluxing a solution of compound 4 (8.23g, 30 mmole) and compound 7 (5.74g, 30 mmole) in 30 mL toluene containing KOH as catalyst for 3 hr, yield 8.05g (82%); m.p. 82-84°C, b.p. 248-49°C/5mm of Hg. AnaL Found: C, 5539; H, 8.75; N, 13.09; Si , 8.72. Calcd for C, sH29N30 3Si: C, 55.0 I; H, 8.93; N, 12.83; Si, 8.57%. IR (KBr) : 2970vs (VasCH3), 2868s (VsCH3), 1665w, 1601s (imidazoline ring), 1461s, 1378m (8CH3C), 1379m, 1330w (wCH2N), 1241 m (wCI-hO), 11 86m ('tCH20), 1152vs, 1114vs (vC-O), 1067s, IOlOw (Va~NC3), 965s (vC-C), 910w (vsNC3), 880s (vC-N), 799s, 761 vs (vasSi-O), 723s, 660vw, 640m (vsSi-O), 570m (Si~N) cm" ; 'H NMR (8, CDCI3): OA5 (t, 2H, SiCH2), 1.13-1.26 (m, 9H, CH3), 1.68 (m, 2H, CCH2C), 2.70-2 .91 (m, 6H, NCH2), 3. 16 (t, 2H, CH2N), 3.72-4.10 (m, 3H , OCH), 3.27 (t , 4H, CH2, J=IO.0 Hz) (imidazoline ring) , 6.93 (s , IH, CH); J3C NMR (8, CDCb): 13 .1 0 (SiCH2), 20.01, 20.11, 20A4, 22.83 (CH3), 24.01 (CCH2C), 43.06 (CH2N), 51.30 (C-5), 55.10 (C-4) (imidazoline ring), 58.52, 61.27,61.37,63 .08,64.12, 64A3, 66-17 , 66.84 (OCH and NCH2), 156.10 (C-2) (imidazoline ring) .

Tris[3-(silatranyl)propyIJisocyanurate Sa. Com­pound Sa was obtained by stirring and refluxing a solution of compound 5 ( 12.32g, 20 mmole) and compound 6 (8.95g, 60 mmole) in 100 mL benzene containing KOH as catalyst for 2 hL yield 14.73g (95 %); m.p. 11 8-20oe AnaL Found : C, 46 .29; H, 6.85; , 11.09; Si , 10.72 . Calcd for C30Hs4N60 '2Si3: C, 46A9; H, 7.02; N, 10.84; Si, 10.87%. IR (KB r): 1686vs (vC=O), 1368m, 1340v w (wCH1N), 1282m (wCH20 ), 11 80w ('tCH20 ), 11 30vs, 1103vs (vC-O), 1050vs, 1023s (VasNC3), 940m (vC-C), 917s (vsNC3), 880w (vC-N), 780vs, 76 1 vs (vasSi -O), 730s, 680vw, 625m (v~S i -O) , 580 m (Si~N) cm"; ' H NMR (8,

CDCl3): 0.38 (t, 6H, SiCHz), 1.60 (m, 6H, CCH2C), 2.78 (t, 18H, NCHz), 3.17 (t, 6H, CHzN), 3.74 (t, 18H, OCHz); J3C NMR (8, CDCI3): 13 .90 (SiCH2), 24.90 (CCH2C), 44.25 (CH2N), 51.20 (NCH2), 57.80 (OCHz), 148.71 (C=O).

Tris[3-(3,7,10-trimethyIsilatranyl)propyIJisocya­nurate 5b. Compound 5b was obtained by stirring and refluxing a solution of compound 5 (9. 17g, 16 mmole) and compound 7 (9.29g, 48 mmole) in 100 mL benzene containing KOH as catalyst for 2 hr. yield 12.26g (85%); m.p. 80~82°e AnaL Found: C, 52.29; H, 7.85; N, 8.19; Si, 9A2. Calcd for C3yHn N60'2Si3 : C, 51 .97; H, 8.05 ; N, 9.32; Si , 9.30%. lR (KBr): 2969vs (vasCH3), 2874s (vsCH3), 1688vs (vC=O), 1463s, 1376m (8CH3C), 1335m (wCH2N), 1270m (wCH20), 1180m ('tCH20), 1156vs, 1112vs (vC-O), 1064s, 1010w (vasNC3), 973s (vC-C), 910vw (vsNC3), 881s (vC-N J, 771 vs, 761 vs (vasSi-O), 125m, 661 w, 610vw (vsSi-O), 577m (Si~N) cm" ; 'H NMR (8, ~DCI3 ): 0.90 (t, 2H, SiCH2), 1.08-1.15 (m, 27H, CH3), 1.81 (m, 6H, CCH2C), 2.09-2A I (m, 18H, NCH2), 3.08 (t, 6H, CH2N), 3.61-3.97 (m, 9H, OCH); '3<;:: NMR (8, CDCb): 14.21 (SiCH2), 20.71, 20.95, 21.21, 23Al (CH3), 24.51 (CCH2C), 46.31 (CH 2N). 59 .08 , 61.83,62.52,63.73, 65A4, 65.59, 66.30, 67 .39 (OCH and CHz), 149.33 (C=O).

AcknowJedgement One of us (SCV) is indebted to DRDO, New Delhi

for the award of Junior/Senior Research Fellowship. The authors also acknowledge the help from the Cen­tre for Analytical Facility, DMSRDE, Kanpur for IR and elemental analyses and Prof. B.L.Khandelwal, Emiritus Scientist, CSIR, for hi s help in recording the NMR spectra on 300 MHz machine. Thanks are al 0

due to the Director, Defence Materi als & Stores Re­search & Development Establi shment, for encour­agement and permission to publish th is work .

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