Matrix isolation and photochemistry of alpha-diazo sulfoxides: Formation of alpha-oxo sulfine as an intermediate

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TY  - JOUR
  - Sander, W,Strehl, A,Maguire, AR,Collins, S,Kelleher, PG
  - 2000
  - September
  - European Journal of Organic Chemistry
  - Matrix isolation and photochemistry of alpha-diazo sulfoxides: Formation of alpha-oxo sulfine as an intermediate
  - Validated
  - ()
  - matrix isolation photochemistry diazo compounds sulfines STABILIZED PHOSPHORUS YLIDES FLASH VACUUM PYROLYSIS CEPHALOSPORINS CARBAPENEMS REACTIVITY GENERATION GEOMETRY
  - 3329
  - 3335
  - The photochemistry of the alpha-diazo sulfoxides la and Ib has been investigated in solid argon at 10 K by IR and UV/Vis spectroscopy. Both diazo compounds react to form sulfine 2a by photochemically induced hetero Wolff rearrangement of sulfinyl carbene 3, which itself cannot be detected in solid argon. Irradiation at lambda > 320 nm results in decomposition of the sulfine 2a to give 2-oxa-4-thiabicyclo[4.4.0]decane-3,5-dione (5) and 7-oxabicyclo[4.2.0]octan-8-one (6) under abstraction of COS. The matrix-isolated species have been identified by comparison of experimental and calculated IR spectra.
DA  - 2000/09
ER  - 
@article{V43338763,
   = {Sander,  W and Strehl,  A and Maguire,  AR and Collins,  S and Kelleher,  PG },
   = {2000},
   = {September},
   = {European Journal of Organic Chemistry},
   = {Matrix isolation and photochemistry of alpha-diazo sulfoxides: Formation of alpha-oxo sulfine as an intermediate},
   = {Validated},
   = {()},
   = {matrix isolation photochemistry diazo compounds sulfines STABILIZED PHOSPHORUS YLIDES FLASH VACUUM PYROLYSIS CEPHALOSPORINS CARBAPENEMS REACTIVITY GENERATION GEOMETRY},
  pages = {3329--3335},
   = {{The photochemistry of the alpha-diazo sulfoxides la and Ib has been investigated in solid argon at 10 K by IR and UV/Vis spectroscopy. Both diazo compounds react to form sulfine 2a by photochemically induced hetero Wolff rearrangement of sulfinyl carbene 3, which itself cannot be detected in solid argon. Irradiation at lambda > 320 nm results in decomposition of the sulfine 2a to give 2-oxa-4-thiabicyclo[4.4.0]decane-3,5-dione (5) and 7-oxabicyclo[4.2.0]octan-8-one (6) under abstraction of COS. The matrix-isolated species have been identified by comparison of experimental and calculated IR spectra.}},
  source = {IRIS}
}
AUTHORSSander, W,Strehl, A,Maguire, AR,Collins, S,Kelleher, PG
YEAR2000
MONTHSeptember
JOURNAL_CODEEuropean Journal of Organic Chemistry
TITLEMatrix isolation and photochemistry of alpha-diazo sulfoxides: Formation of alpha-oxo sulfine as an intermediate
STATUSValidated
TIMES_CITED()
SEARCH_KEYWORDmatrix isolation photochemistry diazo compounds sulfines STABILIZED PHOSPHORUS YLIDES FLASH VACUUM PYROLYSIS CEPHALOSPORINS CARBAPENEMS REACTIVITY GENERATION GEOMETRY
VOLUME
ISSUE
START_PAGE3329
END_PAGE3335
ABSTRACTThe photochemistry of the alpha-diazo sulfoxides la and Ib has been investigated in solid argon at 10 K by IR and UV/Vis spectroscopy. Both diazo compounds react to form sulfine 2a by photochemically induced hetero Wolff rearrangement of sulfinyl carbene 3, which itself cannot be detected in solid argon. Irradiation at lambda > 320 nm results in decomposition of the sulfine 2a to give 2-oxa-4-thiabicyclo[4.4.0]decane-3,5-dione (5) and 7-oxabicyclo[4.2.0]octan-8-one (6) under abstraction of COS. The matrix-isolated species have been identified by comparison of experimental and calculated IR spectra.
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