Pummerer-type rearrangement on aromatic rings: An unprecedented ipso-substitution of the sulfinyl group of p-sulfinylphenyl ethers into oxygen functional groups leading to protected dihydroquinone derivatives

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 22, 1995, Pages 2319-2320

  Akai, Shuji ^a   Iio, Kiyosei ^a   Takeda, Yoshifumi ^a   Ueno, Hiroshi ^a   Yokogawa, Kayoko ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BENZENE DERIVATIVE; ETHER DERIVATIVE; HYDROQUINONE DERIVATIVE; OXYGEN; STYRENE; TRIFLUOROACETIC ACID;

ARTICLE; DRUG SYNTHESIS;

EID: 0028808295     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39950002319     Document Type: Article

References (11)

1. A recent example of ywo-substitution reaction of p-hydroxyphenyl-diazonium salts: N. Yoneda, T. Fukuhara, T. Mizokami and A. Suzuki, Chem. Lett., 1991, 459.
2. R.G.R. Bacon and S.C. Rennison, J. Chem. Soc. (C), 1969, 312.
3. Baeyer-Villiger rearrangement of p-acylphenols has a similar effect on this transformation: recent example: L. Syper, Synthesis, 1989, 167.
4. Examples: K. Shishido, K. Goto, S. Miyoshi, Y. Takaishi and M. Shibuya, J. Org. Chem., 1994, 59, 406.
5. A.V. Rama Rao, A.R. Mehendale and K. Bal Reddy, Tetrahedron Lett., 1983, 24, 1093.
6. Although the ipso-substitution of sulfinyl groups of the aromatic compounds into heterofunctional groups was reported, yields are high only for substrates having strongly electron-withdrawing nitro and sulfonyl groups on the aromatic ring: S. Oae and N. Furukawa, Adv. Heterocycl. Chem., 1990, 48, 1.
7. R.R. King, J. Org. Chem., 1978, 43, 3784.
8. Recently, the two-step /pso-substitution of aromatic sulfinyl groups into phenoxy groups was reported: M.E. Jung, D. Jachiet, S.I. Khan and C. Kim, Tetrahedron Lett., 1995, 36, 361.
9. S. Akai, Y. Takeda, K. Iio, Y. Yoshida and Y. Kita, J. Chem. Soc, Chem. Commun., 1995, 1013.
10. P. Hamel, Y. Girard and J.G. Atkinson, J. Org. Chem., 1992, 57, 2694.
11. T. Morishita, N. Furukawa and S. Oae, Tetrahedron, 1981, 37, 3115.