Molecular rearrangements Stevens rearrangement

For a review, see Stevens, T.S. Watts, W.E. Selected Molecular Rearrangements Van Nostrand-Reinhold Princeton, 1973, p. 192. 

For books, see Mayo, P. de Rearrangements in Ground and Excited States, 3 vols. Academic Press NY, 1980 Stevens, T.S. Watts, W.E. Selected Molecular Rearrangements Van Nostrand-Reinhold Princeton, 1973. For a review of many of these rearrangements, see Collins, C.J. Eastham, J.F. in Patai The Chemistry of the Carbonyl Group, vol. 1 Wiley NY, 1966, p. 761. See also the series Mechanisms of Molecular Migrations. 

Molecular rearrangements such as that of Stevens or the sulfoxide sulfinic acid, Ramberg-Backlund or sultone sultine rearrangements, are quite common in these classes of compounds. 

SHORTER, J. Correlation Analysis in Organic Chemistry (OUP, 1973). STEVENS, T. s. and WATTS, N. E. Selected Molecular Rearrangements (Van Nostrand Reinhold, 1973). 

Sprung Wallis/. Am. Chem. Soc. 1934, 56. 1715. See also Hart Elia/. Am. Chem. Soc. 1954, 76. 3031. For a review, see Stevens Watts Selected Molecular Rearrangements Van Nostrand-Reinhold Princeton, 1973. pp. 192-199. 

Reviews H. Redlich, 1994, Angew. Chem. Int. Ed. Engl., 33, 1345 (b) T.S. Stevens and W.E. Watts, 1973, Selected Molecular Rearrangements, Van Nostrand Reinhold, London. 

Eor a treatise on azides, which includes discussion of rearrangement reactions, see Scriven, E.F.V. Azides and Nitrenes, Academic Press, NY, 1984. For a review of rearrangements of alkyl and aryl azides, see Stevens, T.S. Watts, W.E. Selected Molecular Rearrangements, Van Nostrand-Reinhold, Princeton, NJ, 1973, pp. 45-52. For reviews of the formation of nitrenes from alkyl and aryl azides, see, in Lwowski, W. Nitrenes, Wiley, NY, 1970, the chapters by Lewis, E.D. Saunders, Jr., W.H. pp. 47-97, 47-78 and by Smith, P.A.S. pp. 99-162. 

Thomson, T., Stevens, T. S. Degradation of quaternary ammonium salts. V. Molecular rearrangements in related sulfur compounds. J. Chem. Soc., Abstracts 1932, 69-73. 

Other reactions that are very likely subject to the persistent radical effect are molecular rearrangements such as the Meisenheimer, amineimide, Wit-tig, Stevens, and sulfenate rearrangements of Scheme 20, for which evidence for radical intermediates has been accumulated.77... 

Recent X-ray diffraction studies now seem to have brought some order into the stereochemistry of the tetrabenzo[a,c,q,i] cyclodecane isomers (123) prepared from 122 through the Stevens rearrangement, followed by dehydration of the resulting glycol. Inspection of molecular models indicates that three stereoisomers of C2h, C2, and Da (123) symmetry are possible for the cis-cis combination, but so far only two isomers have been reported, one of C2h symmetry (m.p. 306.5°C) (124), and the other of C2 symmetry (m.p. 253°C). 

Early reviews H. E. Zimmerman in Molecular Rearrangements Part 1, P. de Mayo, Ed. (Wiley-Interscience, New York, 1963) pp 382-391 S. H. Pine, Org. React. 18,403-464 (1970). Extension to sulfur ylides M. Yamamoto et al, Bull. Chem. Soc. Japan 62,958 (1989) H. Ishibashi etal, Chem. Pharm. Bull. 39, 2878 (1991). Effects of aromatic substitution T. Tanaka era/., ibid. 40, 518 (1992). Selectivity studies (Sommelet-Hauser rearrangement vs Stevens rearrangement q.v.) T. Kitano et ah, J. Chem. Soc. Perkin Trans. 11992,2851 T. Tanaka et al, J. Org. Chem. 57, 5034 (1992). Cf. Meisenheimer Rearrangements r2.31-Wittig Rearrangement. 

Stevens rearrangements proceed smoothly whenever a benzylic group is migrating. For example, ethereal phenyllithium readily deprotonates tetramethylammon-ium bromide to give the lithium bromide-complexed ylide. This species reacts with a variety of electrophiles such as benzophenone, methyl iodide, or molecular iodine. But when the suspension is shaken in a sealed tube for 90 h at ambient temperature, the ylide decomposes entirely to trimethylamine and polymethylene (up to 74%) irrespective of the solvent used (DEE, THE, glyme). The same kind of degradation occurs when phenyllithium is replaced by -butyllithium or phenylsodium. ... 

Lepey, A. R., Giumanini, A. G. Stevens and Sommelet rearrangements. Mechanisms of Molecular Migrations 1971, 3, 297-440. 

Lepley AR, Giumanini AG. Stevens and Sommlet rearrangements. In Thygarajan BS,editor. Mechanisms of molecular migrations. Vol. 3. New York Interscience 1971 p 297-440. 

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