Abstract
Allylic sulfonyl halides can be generated by halogenolysis of the corresponding triorganotin sulfinates. Allylic sulfonyl bromides and iodides undergo a first order, thermal desulfination with allylic rearrangement to yield the corresponding allylic halides. The desulfination of a cyclic allylic sulfonyl bromide is stereospecific, proceeding with γ-syn bromine migration.
| Original language | English |
|---|---|
| Pages (from-to) | 4493-4496 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 38 |
| Issue number | 25 |
| DOIs | |
| Publication status | Published - 23 Jun 1997 |
| Externally published | Yes |
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The thermal desulfination of allylic sulfonyl halides. / King, Malcolm D.; Sue, Rodney E.; White, Rodney H.; Young, David J.
In: Tetrahedron Letters, Vol. 38, No. 25, 23.06.1997, p. 4493-4496.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - The thermal desulfination of allylic sulfonyl halides
AU - King, Malcolm D.
AU - Sue, Rodney E.
AU - White, Rodney H.
AU - Young, David J.
PY - 1997/6/23
Y1 - 1997/6/23
N2 - Allylic sulfonyl halides can be generated by halogenolysis of the corresponding triorganotin sulfinates. Allylic sulfonyl bromides and iodides undergo a first order, thermal desulfination with allylic rearrangement to yield the corresponding allylic halides. The desulfination of a cyclic allylic sulfonyl bromide is stereospecific, proceeding with γ-syn bromine migration.
AB - Allylic sulfonyl halides can be generated by halogenolysis of the corresponding triorganotin sulfinates. Allylic sulfonyl bromides and iodides undergo a first order, thermal desulfination with allylic rearrangement to yield the corresponding allylic halides. The desulfination of a cyclic allylic sulfonyl bromide is stereospecific, proceeding with γ-syn bromine migration.
UR - http://www.scopus.com/inward/record.url?scp=0030900460&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(97)00911-8
DO - 10.1016/S0040-4039(97)00911-8
M3 - Article
VL - 38
SP - 4493
EP - 4496
JO - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry
JF - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry
SN - 0040-4039
IS - 25
ER -