Abstract
A series of model compounds were prepared in order to investigate the conditions that would favour the formation of a cyclopropyl carbinyl radical via a 1,5 hydrogen atom translocation process. The models varied in the degree of unsaturation adjacent to the cyclopropyl carbinyl position and it was found that the 1,5 hydrogen atom radical translocation process was favoured only when alternative cyclisation pathways were not possible.
Keywords
References
1.
For leading reference see:
Wolff M.E.
, Chem. Rev. , 1963 , 63 , 55 .
2.
Barton D.H.R.
, Pure Appl. Chem. , 1968 , 16 , 1 .
3.
For leading reference see:
Wiedenfeld D.
, and
Breslow R.
, J. Am. Chem. Soc. , 1991 , 113 , 8977 .
4.
For leading reference see:
Curran D.P.
, and
Shen W.
, J. Am. Chem. Soc. , 1993 , 115 , 6051 .
5.
Lathbury D.C.
,
Parsons P.J.
, and
Pinto I.
, J. Chem. Soc., Chem. Commun. , 1988 , 81 .
6.
Denenmark D.
,
Winkler T.
,
Waldner A.
, and
De Mesmaeker A.
, Tetrahedron Lett. , 1992 , 33 , 3613 .
7.
Griffiths J.
, and
Murphy J.A.
, J. Chem. Soc., Chem. Commun. , 1991 , 1422 .
8.
Rawal V.H.
, and
Iwasa S.
, Tetrahedron Lett. , 1992 , 33 , 4687 .
9.
For leading reference see:
Batey R.A.
,
Harling J.D.
, and
Motherwell W.B.
, Tetrahedron , 1992 , 48 , 8031 .
10.
Jiang B.
,
Chen Z.
, and
Xiong W.
, Chem. Commun. , 2002 , 1524 .
11.
Shibata T.
,
Tabira H.
, and
Soai K.
, J. Chem. Soc., Perkin Trans., 1 1998 , 177 .
12.
Diana G.D.
,
Salvador U.J.
,
Zalay E.S.
,
Johnson R.E.
,
Collins J.C.
,
Johnson D.
,
Hinshaw W.B.
,
Lorenz R.R.
,
Theilking W.H.
, and
Pancic F.
, J. Med. Chem. , 1977 , 20 , 750 .
13.
Chen S-M.L.
,
Schaub R.E.
, and
Grudzinskas C.V.
, J. Org. Chem. , 1978 , 43 , 3450 .
14.
CTAB is cetyltrimethylammonium bromide.
15.
Stork G.
, and
Mook R.
Jr.
, J. Am. Chem. Soc. , 1987 , 109 , 2829 .
16.
Crich D.
, and
Fortt S.M.
, Tetrahedron Lett. , 1987 , 28 , 2895 .
