292
C.P. Casey, S. Chung / Inorganica Chimica Acta 334 (2002) 283Á293
/
Minor isomer (34b): 1H NMR (CD2Cl2, 300 MHz,
(c) H. Kurosawa, S. Ogoshi, Bull. Chem. Soc. Jpn. 71 (1998) 973;
(d) U. Belluco, R. Bertani, R.A. Michelin, M. Mozzon, J.
Organomet. Chem. 600 (2000) 37;
0 8C): 7.15 (q, Jꢂ
/
7 Hz, CHÄ
/
), 2.74 (br s, CÅ/CCH3),
2.35 (d, Jꢂ7 Hz, CH3CHÄ
/
/), 2.10 (s, C5Me5).
(e) J.-T. Chen, Coord. Chem. Rev. 190Á192 (1999) 1143.
/
[2] L.S. Hegedus, Transition Metals in the Synthesis of Complex
Organic Molecules (Chapter 9), University Science Books, Mill
Valley, CA, 1994.
4.17. C5Me5(CO)2Re(h2-PhCÅ
/
CCÅ
/
CPh) (31)
[3] (a) E. Keinan, E. Bosch, J. Org. Chem. 51 (1986) 4006;
(b) Y. Wakatsuki, H. Yamazaki, N. Kumegawa, T. Satoh, J.Y.
Satoh, J. Am. Chem. Soc. 113 (1991) 9604;
A red solution of 1,4-diphenylbutadiyne (500 mg, 2.5
mmol) and 12 (250 mg, 0.56 mmol) in THF (5 ml) was
stirred for 24 h. Volatiles were evaporated under
vacuum and the residue was chromatographed on silica
(c) J. Tsuji, H. Watanabe, I. Minami, I. Shimizu, J. Am. Chem.
Soc. 107 (1985) 2196;
(d) I. Minami, M. Yuhara, H. Watanabe, J. Tsuji, J. Organomet.
Chem. 334 (1987) 225;
gel using 5:1 hexaneÁ
as a bright yellow powder. 1H NMR (CD2Cl2, 300
MHz): d 7.8Á
7.2 (Ph), 2.04 (s, C5Me5). 13C{1H} NMR
/
CH2Cl2 to give 31 (168 mg, 52%)
(e) J. Tsuji, T. Mandai, Angew. Chem., Int. Ed. Engl. 34 (1995)
2589;
/
(CD2Cl2, 126 MHz): d 209.1, 207.0 (CO); 132.1, 131.8,
130.1, 128.9, 128.8, 128.4, 124.5 (Ph); 101.8 (C5Me5);
(f) M.A. Esteruelas, J. Herrero, A.M. Lo´pez, M. Oliva´n,
Organometallics 20 (2001) 3202;
(g) T. Ohmura, S. Yorozuya, Y. Yamamoto, N. Miyaura,
Organometallics 19 (2000) 365.
100.3, 99.6 (bound Å
/
C); 82.3, 67.9 (free Å/C); 10.7
(C5Me5). IR (THF, cmꢁ1): 1962 (s), 1876 (s). EI MS;
Calc. for C28H25O2Re: 580.14. Found: 580.14. Anal.
Calc. for C28H25O2Re: C, 57.99; H, 4.35. Found: C,
58.13; H, 4.39%.
[4] J. Gotzig, H. Otto, H. Werner, J. Organomet. Chem. 287 (1985)
247.
[5] (a) G. Albertin, S. Antoniutti, E. Bordignon, J. Chem. Soc.,
Dalton Trans. (1995) 719;
(b) P. Barbaro, C. Bianchini, M. Peruzzini, A. Polo, F. Zanobini,
P. Frediani, Inorg. Chim. Acta 220 (1994) 5;
(c) M.J. Albe´niz, M.L. Buil, M.A. Esteruelas, A.M. Lo´pez, J.
4.18. C5Me5(CO)2Re[h3-(E)-(PhCHÄ
/
)CCÅ
/
ꢁ
CPh]ꢀBF4 (35)
Organomet. Chem. 545Á546 (1997) 495.
/
[6] (a) G. Jia, J.C. Gallucci, A.L. Rheingold, B.S. Haggerty, D.W.
Meek, Organometallics 10 (1991) 3459;
HBF4×Et2O (0.020 ml, 85%, 0.12 mmol) was syringed
/
(b) C. Bianchini, C. Bohanna, M.A. Esteruelas, P. Frediani, A.
Meli, L.A. Oro, M. Peruzzini, Organometallics 11 (1992) 3837;
(c) S.-M. Yang, M.C.-W. Chan, K.-K. Cheung, C.-M. Che, S.-M.
Peng, Organometallics 16 (1997) 2819;
into a yellow solution of 31 (40 mg, 0.070 mmol) in
CH2Cl2 (5 ml). The resulting dark brown solution was
stirred for 10 min. The solution was then concentrated
under vacuum to 1 ml and condensation of diethyl ether
(d) C. Bianchini, P. Innocenti, M. Peruzzini, A. Romerosa, F.
Zanobini, Organometallics 15 (1996) 272;
(15 ml) at ꢁ78 8C resulted in precipitation of a light
/
(e) G. Jia, A.L. Rheingold, D.W. Meek, Organometallics 8 (1989)
1378;
brown solid, which was filtered at room temperature
and washed with diethyl ether (10 ml) to give 35 as a
1
light brown powder (36 mg, 78%). H NMR (CD2Cl2,
(f) C. Bianchini, M. Peruzzini, F. Zanobini, P. Frediani, A.
Albinati, J. Am. Chem. Soc. 113 (1991) 5453;
(g) G. Albertin, P. Amendola, S. Antoniutti, S. Ianelli, G. Pelizzi,
E. Bordignon, Organometallics 10 (1991) 2876;
(h) G. Albertin, S. Antoniutti, E. Bordignon, F. Cazzaro, S.
Ianelli, G. Pelizzi, Organometallics 14 (1995) 4114;
(i) D.C. Liles, P.F.M. Verhoeven, J. Organomet. Chem. 522
(1995) 33;
300 MHz): d 8.0Á
13C{1H} NMR (CD2Cl2, 126 MHz): 196.2, 194.7 (CO);
134.4 ((PhCH)ÄC), 134.1 (PhCHÄ); 133.9, 132.4, 131.4,
130.6, 129.7, 128.6, 122.3, 121.7 (Ph); 107.8 (C5Me5),
CPh), 10.4 (C5Me5). IR
(CD2Cl2, cmꢁ1): 2036 (s), 1975 (s). FAB MS; Calc.
for C28H26O2Reꢀ: 581.3. Found: 581.3. Anal. Calc. for
C28H26O2ReBF4: C, 50.38; H, 3.93. Found: C, 50.40; H,
3.75%.
/
7.5 (m, Ph), 7.1 (CHÄ
/
), 2.1 (s, C5Me5).
/
/
99.0 (CÅ
/
CPh), 32.2 (C Å
/
(j) C. Bianchini, P. Frediani, D. Masi, M. Peruzzini, F. Zanobini,
Organometallics 13 (1994) 4616.
[7] (a) L.D. Field, A.V. George, G.R. Purches, I.H.M. Slip,
Organometallics 11 (1992) 3019;
(b) A. Hills, D.L. Hughes, M. Jimenez-Tenorio, G.J. Leigh, C.A.
McGeary, A.T. Rowley, M. Bravo, C.E. McKenna, M.-C.
McKenna, J. Chem. Soc., Chem. Commun. (1991) 522;
(c) L.D. Field, A.V. George, T.W. Hambley, Inorg. Chem. 29
(1990) 4565;
Acknowledgements
(d) D.L. Hughes, M. Jimenez-Tenorio, G.J. Leigh, A.T. Rowley,
J. Chem. Soc., Dalton Trans. (1993) 3151.
Financial support from the National Science Founda-
tion is gratefully acknowledged.
[8] A.K. McMullen, J.P. Selegue, J.-G. Wang, Organometallics 10
(1991) 3421.
[9] N.W. Alcock, A.F. Hill, R.P. Melling, A.R. Thompsett, Organo-
metallics 12 (1993) 641.
References
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