Chlorophosphonates: Inexpensive precursors for stereodefined chloro- substituted olefins and unsymmetrical disubstituted acetylenes

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3733-3737

  Muthiah, C ^a   Praveen Kumar, K ^a   Aruna Mani, C ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKENE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0342657702     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991946y     Document Type: Article

References (49)

1. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
2. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
3. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
4. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
5. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
6. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
7. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
8. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
9. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
10. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
11. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
12. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
13. Selected references: (a) Tsai, H.-J., Thenappan, A.; Burton, D J. J. Org. Chem. 1994, 59, 7085. (b) Tanaka, K., Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735. (c) Kojima, S.; Takagi, R.; Akiba, K.-y. J. Am. Chem. Soc. 1997, 119, 5970. (d) Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. (e) Palacios, F., Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146. (f) Ando, K. J. Org. Chem. 1997, 62, 1934. (g) Sanu, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559. (h) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997. (i) Arai, T.; Sasai, H.; Yamaguchi, K., Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. (j) Davis, A. A.; Rosén, J. J.; Kiddle, J. J. Tetrahedron Lett. 1998, 39, 6263. (k) Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757. (l) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-Ola; Rein, T. J. Org. Chem. 1998, 63, 8284. (m) Shen, Y.; Ni, J.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1999, 509.
14. Kumaraswamy, S.; Selvi, R. S.; Kumara Swamy, K. C. Synthesis 1997, 207.
15. For other routes to α-monohalogenophosphonates, see: (a) Green, D.; Elgendy, S.; Patel, G.; Baban, J. A.; Skordalakes, E.; Husman, W.; Kakkar, V. V.; Deadman, J. Tetrahedron 1996, 52, 10215. (b) Iorga, B.; Eymery, F.; Savignac, P. Tetrahedron 1999, 55, 2671.
16. For other routes to α-monohalogenophosphonates, see: (a) Green, D.; Elgendy, S.; Patel, G.; Baban, J. A.; Skordalakes, E.; Husman, W.; Kakkar, V. V.; Deadman, J. Tetrahedron 1996, 52, 10215. (b) Iorga, B.; Eymery, F.; Savignac, P. Tetrahedron 1999, 55, 2671.
17. Kumaraswamy, S.; Kumara Swamy, K. C. Tetrahedron Lett. 1997, 38, 2183.
18. Muthiah, C.; Praveen Kumar, K.; Kumaraswamy, S.; Kumara Swamy, K. C. Tetrahedron 1998, 54, 14315.
19. (a) Pudovik, A. N.; Konovalova, I. V. Synthesis 1979, 81.
20. (b) Engel, R. In Synthesis of Phosphorus-Carbon Bonds; CRC Press: Boca Raton, FL, 1988; pp 101-136.
21. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
22. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
23. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
24. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
25. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
26. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
27. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
28. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
29. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
30. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
31. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
32. Selected references on the synthesis of of disubstituted acetylenes: (a) Zimmer, H.; Bercz, P. J.; Maltenieks, O. J.; Moore, M. W. J. Am. Chem. Soc. 1965, 87, 2777. (b) Zimmer, H.; Hickey, K. R.; Schumacher, R. J. Chimia 1974, 28, 656. (c) Glascoyne, J. M.; Mitchell, P. J.; Philips, L.; J. Chem. Soc., Perkin Trans. 2 1977, 1051. (d) Ishihara, T.; Mackawe, T.; Ando, T. Tetrahedron Lett. 1984, 25, 1377. (e) Gallagher, M. J.; Noerdin, H. Aust. J. Chem. 1985, 38, 997. (f) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. (g) Kondo, K.; Ohnishi, N.; Takemoto, K.; Yoshida, H.; Yoshida, K. J. Org. Chem. 1992, 57, 1622. (h) Kondo, K.; Fujitani, T.; Ohnishi, N.; J. Mater. Chem. 1997, 7, 429. (i) John, J. A., Tour, J. M. Tetrahedron 1997, 53, 15515. (j) Mouries, V., Waschbusch, R.; Carran, J. Savignac, P. Synthesis 1998, 271. (k) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153. (l) Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. J. Chem. Soc., Chem. Commun. 2000, 87. In c, e, g, and h, the route (a) of Zimmer is used.
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