Reactions of δ-carbon radicals generated by 1,5-hydrogen transfer to alkoxyl radicals

Tetrahedron

Volumn 59, Issue 41, 2003, Pages 8073-8090

  Čeković, Živorad ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

1,5 hydrogen transfer; C C bond formation; Intramolecular functionalisation; Radicals and radical reactions

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALKYLBENZENESULFONIC ACID; BENZENE DERIVATIVE; CARBON; HYDROGEN; LEAD; NITRITE; PEROXIDE; RADICAL;

ATOM; CHEMICAL BOND; CHEMICAL REACTION; DECOMPOSITION; OXIDATION; PHOTOLYSIS; PRIORITY JOURNAL; PROTON TRANSPORT; REVIEW; SYNTHESIS;

EID: 0141570904     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01202-X     Document Type: Review

References (125)

1. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
2. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
3. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
4. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
5. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
6. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
7. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
8. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
9. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
10. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
11. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
12. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
13. For leading reviews of reactions of δ,-carbon radicals see: (a) Heusler K., Kalvoda J. Angew. Chem., Int. Ed. Engl. 3:1964;525-538 (b) Mihailović M.L., Čeković Ž. Synthesis. 1970;209-224 (c) Kalvoda J., Heusler K. Synthesis. 1971;501-526 (d) Hesse R.H. Advan. Free Radical Chem. 3:1969;83 (e) Akhtar M. Advan. Photochem. 2:1964;263-303 (f) Brun P., Waegell B. Tetrahedron, (Report No 12). 32:1976;517-526 (g) Barton D.H.R. Pure Appl. Chem. 16:1968;1 (h) Majetich G., Wheless K. Tetrahedron, (Report No 375). 51:1995;7095-7129 (i) Backwith A.L.J.K., Ingold U. de Mayo P. Free Radical Rearrangements in Rearragements in Gound and Excited States. Vol. 1:1980;161-309 Academic, New York, (j) Mihailović M.L., Čeković Ž., Lorenc L. Mijs W.J., de Jonge C.R.H.I. Oxidations with Lead Tetraacetate in Organic Synthesis by Oxidation with Metal Compounds. 1986;758-816 Plenum, New York, (k) Rotermund, G.W., Methoden der Organische Chemie (Houben-weil), Band 4. Teil 1b, Oxidatioin II, pp. 204-220, Ed. Muller, E., George Thieme, Stuttgart. (l) Feray L., Kuznetsov N., Renaud P. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 2:2001;246-277 Wiley-VCH, Weinheim. Ch.3.6 (m) Kropf H., Maher-Detweiler M. Methoden der Organische Chemie (Houben-weil), Band 6/1b, Teil 3. Kropf H. Alcohole III. 1984;590-613 George Thieme, Stuttgart.
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