Synthesis of 1-Aza-8-thiabicyclo[4.2.1]nona-2,4-diene 8,8-dioxide and its conversion to a strained spirocycle via photoinduced SO2-N bond cleavage.
A route to the doubly unsaturated bridgehead sultam 12 has been developed. When irradiated at 350 nm, this conjugated diene is isomerized via a two-photon process to the structurally novel spiro heterocycle 17 constituted of cyclobutene, thietane dioxide, and pyrrolidine rings. A probable mechanism for the generation of 17 and select reactions thereof are reported. [reaction: see text]
Paquette
Leo A
LA
Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210, USA. paquette.1@osu.edu
Barton
William R S
WR
Gallucci
Judith C
JC
D000466:Alkadienes / Q000737:chemistry*; D000818:Animals; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D010777:Photochemistry; D011759:Pyrrolidines / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis*
C496161:1-aza-8-thiabicyclo(4.2.1)nona-2,4-diene 8,8-dioxide; D000466:Alkadienes; D001372:Aza Compounds; D003503:Cyclobutanes; D011759:Pyrrolidines; D013449:Sulfonamides; C032519:pyrrolidine