Lewis Acid-Promoted Reactions of N1,N4-Dibenzoyl-1,4-benzoquinone Diimines with (E)-Propenylbenzenes: An Unexpected Reaction

Journal of Organic Chemistry

Volumn 63, Issue 2, 1998, Pages 314-318

  Engler, Thomas A ^a   Luterman, Dana R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542629739     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971551j     Document Type: Article

References (34)

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12. (f) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693.
13. (g) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
14. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
15. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
16. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
17. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
18. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
19. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
20. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
21. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
22. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
23. Lewis acid-promoted reactions of quinones and imide derivatives with dienes, styrenes, and alkenes have been found to give products of 4 + 2, 5 + 2, 2 + 2, and 3 + 2 cycloaddition, as well as simple alkylation. For examples and leading references, see refs 1 and 2 and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254. (d) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-06. (e) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970. (f) Engler, T. A.; Chai, W.; LaTessa, K. O J. Org. Chem. 1996, 61, 9297-9308. (g) Engler, T. A.; Agrios, K.; Reddy, J. P.; Iyengar, R. Tetrahedron Lett. 1996, 37, 327-330. (h) Murphy, W. S.; Neville, D. Tetrahedron Lett. 1996, 37, 9397-9340. Neville, D.; Murphy, W. S. Tetrahedron Lett. 1996, 37, 5221-5224. (j) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65 and references therein.
24. 2O traps cationic intermediate 11. This made it difficult to judge when reactions were complete.
25. (b) Many crude reaction mixtures contained unreacted propenylbenzene and reduced diimine and were thus routinely subjected to flash chromatography as part of the workup. All fractions were carefully examined for the presence of other stereoisomeric products, to no avail.
26. The X-ray data for this structure have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
27. Adams, R.; Acker, D. S. J. Am. Chem. Soc. 1952, 74, 5872-5876.
28. Nucleophilic attack on nitrogen in unsubstituted benzoquinone diimines has been observed (Brown, E. R. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappaport, Z., Eds.; Wiley: Chichester, 1988; Vol. 2, Part 2, Chapter 21), but this type of reactivity is rare for reactions of N-sulfonyl- or N-benzoylbenzoquinone diimines. Adams reported such products in reactions of aniline with N,N-dibenzoyl-1,4-benzoquinone diimine (Adams, R.; Werbel, L. J. Org. Chem. 1957, 22, 1287-1291) and N,N-bis(phenylsulfonyl)-2,3,5,6-tetrachloro-1,4-benzoquinone diimine (Adams, R.; Braun, B. J. Am. Chem. Soc. 1952, 74, 5869-5871). Contradicting Adams' structural assignment of the products of addition of phenols to N,N-bis(phenylsulfonyl)benzoquinone diimines (Adams, R.; Blomstrom, D. J. Am. Chem. Soc. 1953, 75, 3405-3408), Nishiyama suggested that bond formation occurred at nitrogen rather than carbon (Nishiyama, Y.; Ikagami, Y.; Seto, S. Bull. Chem. Soc. Jpn. 1965, 38, 72-76). For a summary of Adams' work in this area, see ref 3j.
29. Nucleophilic attack on nitrogen in unsubstituted benzoquinone diimines has been observed (Brown, E. R. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappaport, Z., Eds.; Wiley: Chichester, 1988; Vol. 2, Part 2, Chapter 21), but this type of reactivity is rare for reactions of N-sulfonyl- or N-benzoylbenzoquinone diimines. Adams reported such products in reactions of aniline with N,N-dibenzoyl-1,4-benzoquinone diimine (Adams, R.; Werbel, L. J. Org. Chem. 1957, 22, 1287-1291) and N,N-bis(phenylsulfonyl)-2,3,5,6-tetrachloro-1,4-benzoquinone diimine (Adams, R.; Braun, B. J. Am. Chem. Soc. 1952, 74, 5869-5871). Contradicting Adams' structural assignment of the products of addition of phenols to N,N-bis(phenylsulfonyl)benzoquinone diimines (Adams, R.; Blomstrom, D. J. Am. Chem. Soc. 1953, 75, 3405-3408), Nishiyama suggested that bond formation occurred at nitrogen rather than carbon (Nishiyama, Y.; Ikagami, Y.; Seto, S. Bull. Chem. Soc. Jpn. 1965, 38, 72-76). For a summary of Adams' work in this area, see ref 3j.
30. Nucleophilic attack on nitrogen in unsubstituted benzoquinone diimines has been observed (Brown, E. R. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappaport, Z., Eds.; Wiley: Chichester, 1988; Vol. 2, Part 2, Chapter 21), but this type of reactivity is rare for reactions of N-sulfonyl- or N-benzoylbenzoquinone diimines. Adams reported such products in reactions of aniline with N,N-dibenzoyl-1,4-benzoquinone diimine (Adams, R.; Werbel, L. J. Org. Chem. 1957, 22, 1287-1291) and N,N-bis(phenylsulfonyl)-2,3,5,6-tetrachloro-1,4-benzoquinone diimine (Adams, R.; Braun, B. J. Am. Chem. Soc. 1952, 74, 5869-5871). Contradicting Adams' structural assignment of the products of addition of phenols to N,N-bis(phenylsulfonyl)benzoquinone diimines (Adams, R.; Blomstrom, D. J. Am. Chem. Soc. 1953, 75, 3405-3408), Nishiyama suggested that bond formation occurred at nitrogen rather than carbon (Nishiyama, Y.; Ikagami, Y.; Seto, S. Bull. Chem. Soc. Jpn. 1965, 38, 72-76). For a summary of Adams' work in this area, see ref 3j.
31. Nucleophilic attack on nitrogen in unsubstituted benzoquinone diimines has been observed (Brown, E. R. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappaport, Z., Eds.; Wiley: Chichester, 1988; Vol. 2, Part 2, Chapter 21), but this type of reactivity is rare for reactions of N-sulfonyl- or N-benzoylbenzoquinone diimines. Adams reported such products in reactions of aniline with N,N-dibenzoyl-1,4-benzoquinone diimine (Adams, R.; Werbel, L. J. Org. Chem. 1957, 22, 1287-1291) and N,N-bis(phenylsulfonyl)-2,3,5,6-tetrachloro-1,4-benzoquinone diimine (Adams, R.; Braun, B. J. Am. Chem. Soc. 1952, 74, 5869-5871). Contradicting Adams' structural assignment of the products of addition of phenols to N,N-bis(phenylsulfonyl)benzoquinone diimines (Adams, R.; Blomstrom, D. J. Am. Chem. Soc. 1953, 75, 3405-3408), Nishiyama suggested that bond formation occurred at nitrogen rather than carbon (Nishiyama, Y.; Ikagami, Y.; Seto, S. Bull. Chem. Soc. Jpn. 1965, 38, 72-76). For a summary of Adams' work in this area, see ref 3j.
32. Nucleophilic attack on nitrogen in unsubstituted benzoquinone diimines has been observed (Brown, E. R. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappaport, Z., Eds.; Wiley: Chichester, 1988; Vol. 2, Part 2, Chapter 21), but this type of reactivity is rare for reactions of N-sulfonyl- or N-benzoylbenzoquinone diimines. Adams reported such products in reactions of aniline with N,N-dibenzoyl-1,4-benzoquinone diimine (Adams, R.; Werbel, L. J. Org. Chem. 1957, 22, 1287-1291) and N,N-bis(phenylsulfonyl)-2,3,5,6-tetrachloro-1,4-benzoquinone diimine (Adams, R.; Braun, B. J. Am. Chem. Soc. 1952, 74, 5869-5871). Contradicting Adams' structural assignment of the products of addition of phenols to N,N-bis(phenylsulfonyl)benzoquinone diimines (Adams, R.; Blomstrom, D. J. Am. Chem. Soc. 1953, 75, 3405-3408), Nishiyama suggested that bond formation occurred at nitrogen rather than carbon (Nishiyama, Y.; Ikagami, Y.; Seto, S. Bull. Chem. Soc. Jpn. 1965, 38, 72-76). For a summary of Adams' work in this area, see ref 3j.
33. Broos, R.; Anteunis, M. J. O. Bull. Soc. Chim. Belg. 1986, 95, 135-138.
34. Adams has reported 4a as an unstable oil (Adams, R.; Neumiller, H., Jr. J. Am. Chem. Soc. 1957, 79, 3808-3812). In our hands, 4a is obtained as a yellow solid, stable for weeks open to the atmosphere at rt. Experimental procedures for the preparation of 4a are included in the Supporting Information.