Lossen rearrangement

Lossen rearrangement

The Lossen rearrangement is the chemical reaction of a hydroxamic acid 1 with a dehydration agent (such as tosyl chloride) to form the O-derivative 2, which spontaneously rearranges to form an isocyanate 3.Ref|Lossen1872Ref|Lossen1874

Several reviews have been published.Ref|Yale1943Ref|Bauer1974Ref|Shiori1991

Hydroxamic acids are commonly synthesized from their corresponding esters.Ref|Hauser1939

References

# Lossen, W. "Ann." 1872, "161", 347.
# Lossen, W. "Ann." 1874, "175", 271 & 313.
# Yale, H. L. "Chem. Rev." 1943, "33", 209. (Review)
# Bauer, L.; Exner, O. "Angew. Chem. Int. Ed. Engl." 1974, "13", 376. (Review)
# Shiori, T. "Comp. Org. Syn." 1991, "6", 821-825. (Review)
# Hauser, C. R.; Renfrow, Jr., W. B. "Organic Syntheses", Coll. Vol. 2, p.67 (1943); Vol. 19, p.15 (1939). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0067 Article] )

ee also

*Curtius rearrangement
*Hofmann rearrangement
*Schmidt reaction


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